3-(5-Bromo-2-methyl-thiophen-3-yl)-propionitrile → 4-Amino-2-[4-(2-cyanoethyl)-5-methylthiophen-2-yl]-thieno[3,2-c]pyridine-7-carboxylic acid amide

HRID 1268852Notes

Reaction equation

HRID 1268852 reaction equation
[NH2:1][C:2]1[C:7]2[CH:8]=[C:9](Br)[S:10][C:6]=2[C:5]([C:12]([NH2:14])=[O:13])=[CH:4][N:3]=1.Br[C:16]1[S:20][C:19]([CH3:21])=[C:18]([CH2:22][CH2:23][C:24]#[N:25])[CH:17]=1>>[NH2:1][C:2]1[C:7]2[CH:8]=[C:9]([C:16]3[S:20][C:19]([CH3:21])=[C:18]([CH2:22][CH2:23][C:24]#[N:25])[CH:17]=3)[S:10][C:6]=2[C:5]([C:12]([NH2:14])=[O:13])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 184465373-(5-Bromo-2-methyl-thiophen-3-yl)-propionitrileHCID 588407134-Amino-2-Bromothieno[3,2-C]pyridine-7-Carboxamide

Product 1

HCID 588407374-Amino-2-[4-(2-cyanoethyl)-5-methylthiophen-2-yl]-thieno[3,2-c]pyridine-7-carboxylic acid amide

Procedure

62 was prepared from 4-amino-2-bromo-thieno[3,2-c]pyridine-7-carboxylic acid amide 17 and 3-(5-bromo-2-methyl-thiophen-3-yl)-propionitrile 61 as a white solid in a similar manner to the procedure described in Example 14. 1H NMR (400 MHz, d6-DMSO) δ: 2.40 (s, 3H), 2.81 (s, 4H), 7.15 (s, 2H), 7.23 (s, 1H), 7.24 (br s, 1H), 7.70 (s, 1H), 7.80 (br s, 1H), 8.46 (s, 1H). MS (EI) m/z (M+H+) 343.

Sources & evidence

ORD record
ord-457ff2a9f200450f8dc47efbfdca39de
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

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