2-Amino-5-bromopyridine → tert-Butyl {4-[[5-(6-amino-pyridin-3-yl)-2-methoxy-benzyl]-(3-chloro-4,7-difluorobenzo[b]thiophene-2-carbonyl)-amino]-cyclohexyl}-methyl-carbamate

HRID 2389659Notes

Reaction equation

HRID 2389659 reaction equation
[C:1]([N:8]([CH3:42])[CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([CH2:30][C:31]2[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[C:16]([C:18]2[S:22][C:21]3[C:23]([F:28])=[CH:24][CH:25]=[C:26]([F:27])[C:20]=3[C:19]=2[Cl:29])=[O:17])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:43][C:44]1[CH:49]=[CH:48][C:47](Br)=[CH:46][N:45]=1>>[NH2:43][C:44]1[N:45]=[CH:46][C:47]([C:33]2[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:31]([CH:32]=2)[CH2:30][N:15]([C:16]([C:18]2[S:22][C:21]3[C:23]([F:28])=[CH:24][CH:25]=[C:26]([F:27])[C:20]=3[C:19]=2[Cl:29])=[O:17])[CH:12]2[CH2:13][CH2:14][CH:9]([N:8]([CH3:42])[C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:5])[CH3:6])[CH2:10][CH2:11]2)=[CH:48][CH:49]=1

Participants

3

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 596835093-{[[4-(BOC-methyl-amino)-cyclohexyl]-(3-chloro-4,7-difluoro-benzo[b]thiophene-2-carbonyl)-amino]-methyl}-4-methoxy-benzene boronic acid

Product 1

HCID 59683462tert-Butyl {4-[[5-(6-amino-pyridin-3-yl)-2-methoxy-benzyl]-(3-chloro-4,7-difluorobenzo[b]thiophene-2-carbonyl)-amino]-cyclohexyl}-methyl-carbamate

Procedure

Boronic acid 9 (1.10 g, 1.76 mmol) is coupled to 2-amino-5-bromopyridine (365 mg, 2.11 mmol) using Method A to give the title compound.

Sources & evidence

ORD record
ord-69930188131c41598f10c5593a8ab29c
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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