Trifluoroacetic acid → HCID 90370243, compound

HRID 2176050Notes

Reaction equation

[OH:1][CH2:2][CH:3]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=[O:48])[NH:17][C:18]3[S:19][C:20]4[CH2:47][CH2:46][CH2:45][CH2:44][C:21]=4[C:22]=3[C:23](=[O:43])[NH:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]4[CH:38]=[CH:37][C:36]([C:39]([O:41][CH3:42])=[O:40])=[CH:35][CH:34]=4)=[CH:27][CH:26]=3)[CH:11]=2)[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1.C(O)(C(F)(F)F)=O>>[OH:1][CH2:2][CH:3]1[CH2:4][NH:5][CH2:6][CH2:7][N:8]1[CH2:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[C:16]([NH:17][C:18]1[S:19][C:20]2[CH2:47][CH2:46][CH2:45][CH2:44][C:21]=2[C:22]=1[C:23]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:38]=2)=[CH:27][CH:26]=1)=[O:43])=[O:48]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 90370194HCID 90370194, compound

Product 1

HCID 90370243HCID 90370243, compoundYield 92.8%

Procedure

By using 1.71 g of tert-butyl 3-(hydroxymethyl)-4-[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)benzyl]piperazine-1-carboxylate and 17 mL of TFA, a reaction was performed under the conditions similar to Preparation Example 12, thereby obtaining 1.38 g of methyl 4-(2-{4-[({2-[(3-{[2-(hydroxymethyl)piperazin-1-yl]methyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]phenyl}ethyl)benzoate.

Workup

customa reaction was performed under the conditions similar to Preparation Example 12

Sources & evidence

ORD record: ord-24954b1786bd40a2aa95e0a0ba5958dc
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062032B2

Reaction notes

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