Ammonia → 3-[1-(2-Chloro-phenyl)-ethoxy]-5-pyridin-3-yl-thiophene-2-carboxylic acid amide

HRID 533228Notes

Reaction equation

C[O:2][C:3]([C:5]1[S:6][C:7]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[CH:8][C:9]=1[O:10][CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[CH3:12])=O.[NH3:26]>CO>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:11]([O:10][C:9]1[CH:8]=[C:7]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[S:6][C:5]=1[C:3]([NH2:26])=[O:2])[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

3-[1-(2-Chloro-phenyl)-ethoxy]-5-pyridin-3-yl-thiophene-2-carboxylic acid methyl ester (58 mg, 0.16 mmol, 1.0 Eq.) was suspended in 7M NH3 in MeOH (10 mL) and heated to 100° C. in a pressure tube for 3 days. The reaction was allowed to cool to ambient temperature, the solvent removed in vacuo and purified by tritruation with MeOH to give the title compound as an off-white solid (30 mg, 0.08 mmol, 54%); 1H NMR (400 MHz, d-6 DMSO) δ 1.72 (3H, d), 6.00 (1H, q), 7.10 (1H, br s), 7.35-7.52 (5H, m), 7.67 (1H, dd), 7.75 (1H, br s), 7.97-8.01 (1H, m), 8.56 (1H, dd), 8.84 (1H, d).

Workup

temperatureto cool to ambient temperature
customthe solvent removed in vacuo
custompurified by tritruation with MeOH

Sources & evidence

ORD record: ord-7fadc40cccfa4a13b55f4930805e1209
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853244B2

Reaction notes

Loading…