Ammonia → HCID 25119995, compound

HRID 389690Notes

Reaction equation

HRID 389690 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:12][C:13]=2[C:14]([O:16]CC)=O)=[CH:5][CH:4]=1.[NH3:25]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:12][C:13]=2[C:14]([NH2:25])=[O:16])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 44605731HCID 44605731, compound

Product 1

HCID 25119995HCID 25119995, compoundYield 16%

Conditions

Temperature
150 °C

Procedure

A suspension of ethyl 4-(4-methoxyphenyl)-2-phenyl-1H-imidazole-5-carboxylate (0.078 g, 0.23 mmol) in aqueous (28%) ammonia (4.5 ml) was heated in the microwave for 35 minutes at 150° C. The solvent was then removed in vacuo and the residue was purified by preparative HPLC to afford 4-(4-methoxyphenyl)-2-phenyl-1H-imidazole-5-carboxamide (0.0109 g, 0.04 mmol, 16%) as a white solid. 1H NMR (DMSO) δ 3.82 (3H, s), 7.01 (2H, d), 7.10 (1H, br. s), 7.39-7.43 (2H, m), 7.49 (2H, dd), 7.85 (2H, d), 8.10 (2H, m). LCMS (2) Rt: 2.46 min; m/z (ES+) 294.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-fdd33967dd3746be83ff0995fad40c7c
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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