Ammonium Chloride → HCID 66965768, compound

HRID 1514888Notes

Reaction equation

HRID 1514888 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:30]=[CH:29][C:15]3[N:16]=[C:17]([C:19]4[C:24]([CH3:25])=[CH:23][C:22]([C:26]#[N:27])=[CH:21][C:20]=4[CH3:28])[NH:18][C:14]=3[CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[N-:31]=[N+:32]=[N-:33].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:30]=[CH:29][C:15]3[N:16]=[C:17]([C:19]4[C:20]([CH3:28])=[CH:21][C:22]([C:26]5[N:31]=[N:32][NH:33][N:27]=5)=[CH:23][C:24]=4[CH3:25])[NH:18][C:14]=3[CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 66965551HCID 66965551, compound

Product 1

HCID 66965768HCID 66965768, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(4-Cyano-2,6-dimethyl-phenyl)-3H-benzoimidazole-5-carboxylic acid (3,4-dimethyl-phenyl)-amide (40 mg), NaN3 (65 mg) and NH4Cl (54 mg) in DMF (1 mL) was heated at 120° C. under microwave radiation for 60 min. The mixture was concentrated under reduced pressure. The crude product was purified by reverse phase column chromatography (C18, H2O:CH3CN=100:0 to 70:30) to give 2-[2,6-dimethyl-4-(2H-tetrazol-5-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid (3,4-dimethyl-phenyl)-amide as a white solid: MS (m/z) 438 (M+1).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe crude product was purified by reverse phase column chromatography (C18, H2O:CH3CN=100:0 to 70:30)

Sources & evidence

ORD record
ord-efb500e44b744739950614712c5d82f1
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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