3-Bromo-2-methoxythiophene → 4-Amino-2-(2-methoxy-thiophen-3-yl)-thieno[3,2-c]pyridine-7-carboxylic acid amide

HRID 1868323Notes

Reaction equation

HRID 1868323 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[O:7][CH3:8].[NH2:9][C:10]1[C:15]2[CH:16]=[C:17](Br)[S:18][C:14]=2[C:13]([C:20]([NH2:22])=[O:21])=[CH:12][N:11]=1>>[NH2:9][C:10]1[C:15]2[CH:16]=[C:17]([C:2]3[CH:6]=[CH:5][S:4][C:3]=3[O:7][CH3:8])[S:18][C:14]=2[C:13]([C:20]([NH2:22])=[O:21])=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 104651873-Bromo-2-methoxythiopheneHCID 588407134-Amino-2-Bromothieno[3,2-C]pyridine-7-Carboxamide

Product 1

HCID 588407554-Amino-2-(2-methoxy-thiophen-3-yl)-thieno[3,2-c]pyridine-7-carboxylic acid amide

Procedure

92 was prepared from 3-bromo-2-methoxythiophene 91 (Zhang, Y.; Hornfeldt, A.-B.; Gronowitz, S.; Stalhandske, C. Acta Chemica Scand. 1994, 48, 843-849) and 4-amino-2-bromo-thieno[3,2-c]pyridine-7-carboxylic acid amide in a similar manner to that described for Example 14. 1H NMR (400 MHz, d6-DMSO) δ: 4.10 (s, 3H), 7.13 (d, J6.0 Hz, 1H), 7.28 (d, J6.0 Hz, 1H), 7.69-7.78 (br s, 1H), 8.19 (s, 1H), 8.20-8.30 (br s, 1H), 8.40 (s, 1H), 8.60-8.80 (br s, 2H). MS (EI) m/z (M+H+) 306, (2M+H+) 611.

Sources & evidence

ORD record
ord-4430dbad507b400aa9a0dda59af66235
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

Loading…