2-Chlorophenyl-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetamide → (S)-2-(2-chloro-phenyl)(4,5,6,7-tetrahydrothieno[3,2-c]pyrid-5-yl)acetamide (+)-camphor sulfonic acid salt

HRID 988861Notes

Reaction equation

HRID 988861 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:12]1[CH2:17][CH2:16][C:15]2[S:18][CH:19]=[CH:20][C:14]=2[CH2:13]1)[C:9]([NH2:11])=[O:10].O.[C@:22]12([CH2:32][S:33]([OH:36])(=[O:35])=[O:34])[C:29]([CH3:31])([CH3:30])[CH:26]([CH2:27][CH2:28]1)[CH2:25][C:23]2=[O:24]>CC(C)=O>[C:22]12([CH2:32][S:33]([OH:36])(=[O:34])=[O:35])[C:29]([CH3:31])([CH3:30])[CH:26]([CH2:27][CH2:28]1)[CH2:25][C:23]2=[O:24].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([N:12]1[CH2:17][CH2:16][C:15]2[S:18][CH:19]=[CH:20][C:14]=2[CH2:13]1)[C:9]([NH2:11])=[O:10]

Participants

4

Reactant 2

HCID 113128242-Chlorophenyl-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetamideHCID 87205896[(1S)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-YL]methanesulfonic acid hydrate

Product 1

HCID 131724104(S)-2-(2-chloro-phenyl)(4,5,6,7-tetrahydrothieno[3,2-c]pyrid-5-yl)acetamide (+)-camphor sulfonic acid saltYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5 g (16.31 mmol) of (±)-(2-chloro-phenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl) acetamide (prepared as given in Examples 10-15) and 4.15 g (16.2 mmol) (1S)-(+)-camphor-10-sulphonic acid monohydrate in 100 mL acetone was kept warm for 20 hrs followed by storing it in temperature below 10° C. A few crystals appeared, the mother liquor was concentrated further and repeated recrystallization, followed by storage in cold condition for few days gave 3.1 g (70% yield) of (S)-2-(2-chloro-phenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyrid-5-yl)acetamide (+)-camphor sulfonic acid salt. The salt was further purified by recrystallization in acetone, until constant specific optical rotation was obtained.

Workup

  1. customin temperature below 10° C
  2. concentrationthe mother liquor was concentrated further
  3. customrecrystallization
  4. waitfollowed by storage in cold condition for few days

Sources & evidence

ORD record
ord-5d84c9d99f4e45b3847fdd244a7c7e9b
Source dataset
uspto-grants-2003_10
Patent number
US06635763B2

Reaction notes

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