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

HRID 1930793Notes

Reaction equation

C[O:2][C:3]([C:5]1[S:6][C:7]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]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.C(OCC)C.[NH3:30]>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]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)[S:6][C:5]=1[C:3]([NH2:30])=[O:2])[CH3:12]

Participants

Conditions

Temperature: 80 °C

Procedure

3-[1-(2-Chloro-phenyl)-ethoxy]-5-imidazol-1-yl-thiophene-2-carboxylic acid methyl ester (265 mg, 0.73 mmol, 1.0 Eq.) was suspended in 7M NH3 in MeOH (10 mL) and heated to 80° C. in a pressure tube for 3 days. The solvent was removed in vacuo and the product isolated by column chromatography (2% to 5% MeOH/EtOAc) followed by trituration from diethyl ether to give the title compound as cream powder (163 mg, 0.47 mmol, 64%); 1H NMR (400 MHz, d-6 DMSO) δ 1.71 (3H, d), 5.89 (1H, q), 7.03 (1H, br s), 7.11 (1H, s), 7.23 (1H, s), 7.36-7.42 (2H, m), 7.49 (1H, dd), 7.63 (1H d), 7.66 (1H, dd), 7.78 (1H, br s), 8.17 (1H, s)

Workup

customThe solvent was removed in vacuo
customthe product isolated by column chromatography (2% to 5% MeOH/EtOAc)

Sources & evidence

ORD record: ord-5249cab25ca24f08ba90c8abeef4849c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188134B2

Reaction notes

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