3-Chloro-4,7-difluorobenzo[b]thiophene-2-carbonyl chloride → HCID 25025839, compound

HRID 2389684Notes

Reaction equation

HRID 2389684 reaction equation
C(O[C:6](=O)[N:7]([CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][CH2:16][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][C:24]=3[F:29])[CH:20]=[CH:19][C:18]=2[O:30][CH3:31])[CH2:11][CH2:10]1)C)(C)(C)C.[Cl:33][C:34]1[C:35]2[C:45]([F:46])=[CH:44][CH:43]=[C:42]([F:47])[C:36]=2[S:37][C:38]=1[C:39](Cl)=[O:40]>>[F:29][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][C:23]=1[C:21]1[CH:20]=[CH:19][C:18]([O:30][CH3:31])=[C:17]([CH:22]=1)[CH2:16][N:15]([CH:12]1[CH2:11][CH2:10][CH:9]([NH:7][CH3:6])[CH2:14][CH2:13]1)[C:39]([C:38]1[S:37][C:36]2[C:42]([F:47])=[CH:43][CH:44]=[C:45]([F:46])[C:35]=2[C:34]=1[Cl:33])=[O:40]

Participants

3

Reactant 2

HCID 219384153-Chloro-4,7-difluorobenzo[b]thiophene-2-carbonyl chlorideHCID 59683487HCID 59683487, compound

Product 1

HCID 25025839HCID 25025839, compound

Procedure

Following the synthetic protocol described in Method D′; 3-Chloro-4,7-difluoro-benzo[b]thiophene-2-carboxylic acid [5-(3-fluoro-pyridin-4-yl)-2-methoxy-benzyl]-(4-methylamino-cyclohexyl)-amide is prepared starting from {4-[5-(3-Fluoro-pyridin-4-yl)-2-methoxy-benzylamino]-cyclohexyl}-methyl-carbamic acid tert-butyl ester and 3-Chloro-4,7-difluoro-benzo[b]thiophene-2-carbonyl chloride. The desired product is isolated in 54%.

Workup

  1. custom3-Chloro-4,7-difluoro-benzo[b]thiophene-2-carboxylic acid [5-(3-fluoro-pyridin-4-yl)-2-methoxy-benzyl]-(4-methylamino-cyclohexyl)-amide is prepared

Sources & evidence

ORD record
ord-eff3c94ff7eb4b3da87d4931768314d1
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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