Ammonium Chloride → HCID 59320820, compound

HRID 341200Notes

Reaction equation

HRID 341200 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:13]=[C:14]([NH:18][C:19]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[O:20])[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:11]=[C:5]2[CH:4]=1)#[N:2].[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+]>CN(C=O)C>[N:2]1[NH:27][N:28]=[N:29][C:1]=1[C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:13]=[C:14]([NH:18][C:19]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[O:20])[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:11]=[C:5]2[CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 59320900HCID 59320900, compound

Product 1

HCID 59320820HCID 59320820, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1-[3-(7-Cyano-imidazo[1,2-a]pyridin-3-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea (65 mg, 0.18 mmol), sodium azide (14 mg, 0.19 mmol) and ammonium chloride (11 mg, 0.20 mmol) were dissolved in DMF (2 ml) and heated at 90° C. for 18 h. The reaction mixture was cooled, the solvent removed in vacuo and the crude reaction mixture purified using reverse phase HPLC. This afforded the title compound as a white solid (14 mg). MS: [M+H]+ 403.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent removed in vacuo
  3. customthe crude reaction mixture
  4. custompurified

Sources & evidence

ORD record
ord-d21dc3777cd64356b73fe60572fdae6a
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

Loading…