HCID 22080627, compound → HCID 90370099, compound

HRID 2176055Notes

Reaction equation

HRID 2176055 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][CH:41]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[CH2:38][CH2:37][CH2:36][CH2:35][C:12]=2[C:13]=1[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)=[O:15])=[O:7].C[O:43][C:44](=[O:52])[CH2:45][NH:46][CH:47]([CH2:50][CH3:51])[CH2:48][CH3:49]>>[C:44]([CH2:45][N:46]([CH2:2][C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][CH:41]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[CH2:38][CH2:37][CH2:36][CH2:35][C:12]=2[C:13]=1[C:14]([NH:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=2)=[CH:21][CH:22]=1)=[O:15])=[O:7])[CH:47]([CH2:50][CH3:51])[CH2:48][CH3:49])([OH:52])=[O:43]

Participants

3

Reactant 2

HCID 22080627HCID 22080627, compoundHCID 90370193HCID 90370193, compound

Product 1

HCID 90370099HCID 90370099, compoundYield 25.1%

Procedure

By using 23 mg of methyl 4-[2-(4-{[(2-{[3-(chloromethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate and 19 mg of methyl[(1-ethylpropyl)amino]acetate as starting materials, alkylation was performed under the conditions similar to Preparation Example 30, and then hydrolysis was performed under the conditions similar to Example 6, thereby obtaining 6.7 mg of 4-(2-{4-[({2-[(3-{[(carboxymethyl)(pentan-3-yl)amino]methyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]phenyl}ethyl)benzoic acid.

Workup

  1. customwas performed under the conditions similar to Preparation Example 30
  2. customhydrolysis

Sources & evidence

ORD record
ord-284ab43af6a9407a972899490bca3b39
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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