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CAS 611-19-8

2-Chlorobenzyl chloride

Codes: Clarithromycin-013, (Ia)91353-6-a, Ticlopidine-002

Application context (from source-drug indications)

Marginal zone B-cell lymphomaClarithromycin/Rabeprazole Sodium/AmoxicillinDuodenal ulcerClarithromycin/Rabeprazole Sodium/AmoxicillinImmune thrombocytopenic purpuraClarithromycin/Rabeprazole Sodium/AmoxicillinGastric ulcerClarithromycin/Rabeprazole Sodium/AmoxicillinGastritisClarithromycin/Rabeprazole Sodium/AmoxicillinHelicobacter pylori infectionClarithromycin/Rabeprazole Sodium/AmoxicillinBack painDiclofenac Sodium/Eperisone HydrochlorideArterial occlusive diseaseTiclopidine Hydrochloride/Ginkgo Biloba Leaf Dried ExtractCerebrovascular diseaseTiclopidine Hydrochloride/Ginkgo Biloba Leaf Dried ExtractEmbolism and thrombosisTiclopidine Hydrochloride/Ginkgo Biloba Leaf Dried ExtractCarotid artery stenosisTiclopidine Hydrochloride/Ginkgo Biloba Leaf Dried ExtractSinusitisClarithromycinTonsillitisClarithromycinAcute bronchitisClarithromycinChronic bronchitisClarithromycinLower respiratory tract infectionClarithromycinPharyngitisClarithromycinOsteoarthritisDiclofenac SodiumRheumatoid arthritisDiclofenac SodiumAnkylosing spondylitisDiclofenac SodiumCommon bile duct diseaseDiclofenac SodiumDental pulp diseaseDiclofenac SodiumArthritisDiclofenac SodiumThromboembolismTiclopidine HydrochlorideArterial occlusive diseaseTiclopidine HydrochlorideTransient ischaemic attackTiclopidine HydrochlorideIntracranial vasospasmTiclopidine HydrochlorideCerebrovascular diseaseTiclopidine HydrochlorideSubarachnoid haemorrhageTiclopidine Hydrochloride

Source drugs (routes using this intermediate)

DrugTierExpiry
Clarithromycin/Rabeprazole Sodium/AmoxicillinTier C — Watch / trade-
Diclofenac Sodium/Eperisone HydrochlorideTier C — Watch / trade-
Ticlopidine Hydrochloride/Ginkgo Biloba Leaf Dried ExtractTier C — Watch / trade-
ClarithromycinTier C — Watch / trade-
Diclofenac SodiumTier C — Watch / trade-
Ticlopidine HydrochlorideTier C — Watch / trade-

Position in synthesis routes (up/downstream chain)

Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.

Clarithromycin/Rabeprazole Sodium/AmoxicillinOptimised routesteps: 5total yield: 4.2g(Clarithromycin (Free))
(3R,4S,5S,6R,7R,9R,10Z,11S,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-14-ethyl-7,12,13-trihydroxy-10-(hydroxyimino)-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one→2-Chlorobenzyl chloride→(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydropyran-2-yloxy]-14-ethyl-7,12,13-trihydroxy-4- [(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione 10-[O-(2-chlorobenzyl)oxime]→Acetic acid (2S,3R,4S,6R)-2-[((3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-10-[[(2-chlorobenzyl)oxy]imino]-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yl)oxy]-4-(dimethylamino)-6-methyltetrahydropyran-3-yl ester→Benzoic acid (2S,3R,4S,6R)-2-[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-10-[[(2-chlorobenzyloxy]imino]-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yloxy]-4-(dimethylamino)-6-methyltetrahydropyran-3-yl ester→Acetic acid (2S,3R,4S,6R)-2-[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-10-[[(2-chlorobenzyloxy]imino]-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yloxy]-4-(dimethylamino)-6-methyltetrahydropyran-3-yl ester→Benzoic acid (2S,3R,4S,6R)-2-[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-10-[[2-chlorobenzyloxy]imino]-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yloxy]-4-(dimethylamino)-6-methyltetrahydropyran-3-yl ester→(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydropyran-2-yloxy]-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione 10-[O-(2-chlorobenzyl)oxime]
Diclofenac Sodium/Eperisone HydrochlorideOptimised routesteps: 3total yield: /
2-Chlorobenzyl chloride→1-(Bromomethyl)-2-chlorobenzene→Formic acid→(2-Chlorophenyl)acetic acid→1-Chloranyl-2-methylbenzene→2,6-Dichloroaniline→2-[2-(2,6-Dichlorophenylamino)phenyl]acetic acid
Ticlopidine Hydrochloride/Ginkgo Biloba Leaf Dried ExtractOptimised routesteps: 3total yield: /
4,5,6,7-Tetrahydrothieno[3,2-c]pyridine→2-Chlorobenzyl chloride→thieno[3,2-c]pyridine→5-[(2-chlorophenyl)methyl]thieno[3,2-c]pyridin-5-ium chloride
ClarithromycinOptimised routesteps: 5total yield: 4.2g(Clarithromycin (Free))
(3R,4S,5S,6R,7R,9R,10Z,11S,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-14-ethyl-7,12,13-trihydroxy-10-(hydroxyimino)-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one→2-Chlorobenzyl chloride→(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydropyran-2-yloxy]-14-ethyl-7,12,13-trihydroxy-4- [(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione 10-[O-(2-chlorobenzyl)oxime]→Acetic acid (2S,3R,4S,6R)-2-[((3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-10-[[(2-chlorobenzyl)oxy]imino]-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yl)oxy]-4-(dimethylamino)-6-methyltetrahydropyran-3-yl ester→Benzoic acid (2S,3R,4S,6R)-2-[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-10-[[(2-chlorobenzyloxy]imino]-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yloxy]-4-(dimethylamino)-6-methyltetrahydropyran-3-yl ester→Acetic acid (2S,3R,4S,6R)-2-[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-10-[[(2-chlorobenzyloxy]imino]-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yloxy]-4-(dimethylamino)-6-methyltetrahydropyran-3-yl ester→Benzoic acid (2S,3R,4S,6R)-2-[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-10-[[2-chlorobenzyloxy]imino]-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yloxy]-4-(dimethylamino)-6-methyltetrahydropyran-3-yl ester→(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydropyran-2-yloxy]-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione 10-[O-(2-chlorobenzyl)oxime]
Diclofenac SodiumOptimised routesteps: 3total yield: /
2-Chlorobenzyl chloride→1-(Bromomethyl)-2-chlorobenzene→Formic acid→(2-Chlorophenyl)acetic acid→1-Chloranyl-2-methylbenzene→2,6-Dichloroaniline→2-[2-(2,6-Dichlorophenylamino)phenyl]acetic acid
Ticlopidine HydrochlorideOptimised routesteps: 3total yield: /
4,5,6,7-Tetrahydrothieno[3,2-c]pyridine→2-Chlorobenzyl chloride→thieno[3,2-c]pyridine→5-[(2-chlorophenyl)methyl]thieno[3,2-c]pyridin-5-ium chloride

Intermediates available on this site

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