Ammonia → HCID 59240243, compound

HRID 1673051Notes

Reaction equation

HRID 1673051 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:36])([F:35])[F:34])[N:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=3)=[CH:13][CH:12]=2)[CH:10]=1)=[O:5])C.[C-]#[N:38].[Na+].N>CO>[CH3:26][S:23]([C:19]1[CH:18]=[C:17]([C:14]2[CH:13]=[CH:12][C:11]([N:9]3[CH:10]=[C:6]([C:4]([NH2:38])=[O:5])[N:7]=[C:8]3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:34])([F:36])[F:35])=[CH:16][CH:15]=2)[CH:22]=[CH:21][CH:20]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8929Sodium CyanideHCID 59240098HCID 59240098, compound

Product 1

HCID 59240243HCID 59240243, compoundYield 316.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl-1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H imidazole-4-carboxylate (500 mg, 0.971 mmol), NaCN (10 mg, 0.194 mmol) and 6 mL 2M NH3 in MeOH were added to a 15 mL sealed tube and heated at 60° C. for 72 h. The reaction was cooled and the compound was absorbed on to silica purified by column chromatography using hexanes:ethyl acetate as eluents to afford 1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazole-4-carboxamide (298 mgs, 63%) as a white solid. 1H-NMR (DMSO, 400 MHz) δ 8.14-8.13 (m, 2H), 8.04-8.01 (m, 1H), 7.92-7.89 (m 1H), 7.85-7.80 (m, 3H), 7.74-7.65 (m, 4H), 7.45 (s, 1H), 7.37-7.35 (m, 2H), 7.27 (s, 1H), 3.28 (s, 3H); MS (ES): 486.1 [M+H]+ and 508.3 [M+Na]+.

Workup

  1. customsealed tube
  2. temperatureThe reaction was cooled
  3. customthe compound was absorbed on to silica
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-69eda0880c0544978a72192d9f7c4a46
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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