Ethyl 4-(cyclopropylamino)cyclohexanecarboxylate → HCID 90370059, compound

HRID 2176052Notes

Reaction equation

HRID 2176052 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:34]=[CH:35][CH:36]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[CH2:33][CH2:32][CH2:31][CH2:30][C:12]=2[C:13]=1[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)=[O:15])=[O:7].[CH:37]1([NH:40][CH:41]2[CH2:46][CH2:45][CH:44]([C:47]([O:49]CC)=[O:48])[CH2:43][CH2:42]2)[CH2:39][CH2:38]1>>[ClH:1].[ClH:1].[CH:37]1([N:40]([CH2:2][C:3]2[CH:36]=[CH:35][CH:34]=[C:5]([C:6](=[O:7])[NH:8][C:9]3[S:10][C:11]4[CH2:33][CH2:32][CH2:31][CH2:30][C:12]=4[C:13]=3[C:14](=[O:15])[NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[CH:4]=2)[CH:41]2[CH2:46][CH2:45][CH:44]([C:47]([OH:49])=[O:48])[CH2:43][CH2:42]2)[CH2:38][CH2:39]1

Participants

3

Reactant 2

HCID 67126892Ethyl 4-(cyclopropylamino)cyclohexanecarboxylateHCID 90370252HCID 90370252, compound

Product 1

HCID 90370059HCID 90370059, compoundYield 91.5%

Procedure

By using 400 mg of 2-{[3-(chloromethyl)benzoyl]amino}-N-[4-(pyridin-4-ylmethyl)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide and 819 mg of ethyl 4-(cyclopropylamino)cyclohexanecarboxylate, the alkylation similar to Preparation Example 30 was performed, and then hydrolysis was performed under the conditions similar to Example 5, thereby obtaining 261 mg of 4-(cyclopropyl{3-[(3-{[4-(pyridin-4-ylmethyl)phenyl]carbamoyl}-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)carbamoyl]benzyl}amino)cyclohexane carboxylic acid dihydrochloride.

Workup

  1. customthe alkylation similar to Preparation Example 30
  2. customhydrolysis

Sources & evidence

ORD record
ord-4273aae7ed744889b4370a863785079b
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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