Ammonium Hydroxide → HCID 57377260, compound

HRID 1258899Notes

Reaction equation

HRID 1258899 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]([CH3:27])[C:12]=1[C:13]1[N:14]=[CH:15][N:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][N:19]=2)[CH:17]=1.C1N=C[N:30](C(N2C=NC=C2)=O)C=1.[OH-].[NH4+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]([CH3:27])[C:12]=1[C:13]1[N:14]=[CH:15][N:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([NH2:30])=[O:23])=[CH:20][N:19]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 57378905HCID 57378905, compound

Product 1

HCID 57377260HCID 57377260, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-(4-(4-(2-fluorophenyl)-1-methyl-1H-1,2,3-triazol-5-yl)-1H-imidazol-1-yl)nicotinic acid (69 mg, 0.189 mmol) in DMF (3 mL) was added CDI (37 mg, 0.227 mmol) and the resulting mixture stirred at 60° C. for 1 h. After cooling to room temperature ammonium hydroxide (300 μL, 1.9 mmol) was added and reaction mixture was stirred for 1 h and then evaporated. Purification by chromatography (reverse phase HPLC) afforded the title compound (56 mg, 81%) as a white foam. MS: m/e=364.1 [M+H]+.

Workup

  1. additionwas added
  2. customreaction mixture
  3. stirringwas stirred for 1 h
  4. customevaporated
  5. customPurification by chromatography (reverse phase HPLC)

Sources & evidence

ORD record
ord-a7473cc18d6847a3bc712bc04d040281
Source dataset
uspto-grants-2013_06
Patent number
US08466181B2

Reaction notes

Loading…