Ethyl bromoacetate → HCID 90377712, compound

HRID 2176049Notes

Reaction equation

[CH:1]1([N:4]([CH2:11][C:12]2[CH:13]=[C:14]([CH:41]=[CH:42][CH:43]=2)[C:15]([NH:17][C:18]2[S:19][C:20]3[CH2:40][CH2:39][CH2:38][CH2:37][C:21]=3[C:22]=2[C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:28][CH:27]=2)=[O:24])=[O:16])[CH:5]2[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:3][CH2:2]1.Br[CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47]>>[CH2:49]([O:48][C:46](=[O:47])[CH2:45][N:8]1[CH2:7][CH2:6][CH:5]([N:4]([CH:1]2[CH2:3][CH2:2]2)[CH2:11][C:12]2[CH:43]=[CH:42][CH:41]=[C:14]([C:15](=[O:16])[NH:17][C:18]3[S:19][C:20]4[CH2:40][CH2:39][CH2:38][CH2:37][C:21]=4[C:22]=3[C:23](=[O:24])[NH:25][C:26]3[CH:27]=[CH:28][C:29]([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:30][CH:31]=3)[CH:13]=2)[CH2:10][CH2:9]1)[CH3:50]

Participants

Reactant 2

HCID 7748Ethyl bromoacetate

HCID 90370179HCID 90370179, compound

Product 1

HCID 90377712HCID 90377712, compoundYield 79.7%

Procedure

By using 340 mg of 2-[(3-{[cyclopropyl(piperidin-4-yl)amino]methyl}benzoyl)amino]-N-[4-(diethylamino)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide and 99 mg of ethyl bromoacetate, a reaction was performed under the conditions similar to Preparation Example 30, thereby obtaining 310 mg of ethyl[4-(cyclopropyl {3-[(3-{[4-(diethylamino)phenyl]carbamoyl}-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)carbamoyl]benzyl}amino)piperidin-1-yl]acetate.

Workup

customa reaction was performed under the conditions similar to Preparation Example 30

Sources & evidence

ORD record: ord-c8b3c956dba0409c8e44ea73a6f2a089
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062032B2

Reaction notes

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