5-Bromopyrimidine → 3-Chloro-benzo[b]thiophene-2-carboxylic acid (2-ethoxy-5-pyrimidin-5-yl-benzyl)-(4-methylamino-cyclohexyl)-amide dihydrochloride

HRID 2389606Notes

Reaction equation

[C:1]([N:8](C)[CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([CH2:28][C:29]2[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][C:34]=2[O:35][CH2:36][CH3:37])[C:16]([C:18]2[S:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[C:19]=2[Cl:27])=[O:17])[CH2:11][CH2:10]1)(OC(C)(C)C)=O.Br[C:43]1[CH:44]=[N:45][CH:46]=[N:47][CH:48]=1>>[ClH:27].[ClH:27].[CH2:36]([O:35][C:34]1[CH:33]=[CH:32][C:31]([C:43]2[CH:44]=[N:45][CH:46]=[N:47][CH:48]=2)=[CH:30][C:29]=1[CH2:28][N:15]([CH:12]1[CH2:11][CH2:10][CH:9]([NH:8][CH3:1])[CH2:14][CH2:13]1)[C:16]([C:18]1[S:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[C:19]=1[Cl:27])=[O:17])[CH3:37]

Participants

Reactant 2

HCID 783445-Bromopyrimidine

HCID 596834943-{[[4-(BOC-methyl-amino)-cyclohexyl]-(3-chloro-benzo[b]thiophene-2-carbonyl)-amino]-methyl}-4-ethoxy-benzene boronic acid

Product 1

HCID 866189703-Chloro-benzo[b]thiophene-2-carboxylic acid (2-ethoxy-5-pyrimidin-5-yl-benzyl)-(4-methylamino-cyclohexyl)-amide dihydrochloride

Procedure

The title compound is prepared from boronic acid 12 (25 mg, 42 μmol) and 5-bromopyrimidine (5.5 mg, 35 μmol) in accordance with Method L2.

Sources & evidence

ORD record: ord-2d80913f06334b51af2b18c07de476f7
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273747B2

Reaction notes

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