Ammonium Hydroxide → HCID 57377694, compound

HRID 1258930Notes

Reaction equation

HRID 1258930 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[N:14]=[CH:15][N:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][N:19]=3)[CH:17]=2)=[C:11]([CH3:27])[N:10]=[N:9]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[N:8]1[C:12]([C:13]2[N:14]=[CH:15][N:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH2:30])=[O:24])=[CH:20][N:19]=3)[CH:17]=2)=[C:11]([CH3:27])[N:10]=[N:9]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 679551606-(4-(1-(2-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)-1H-imidazol-1-yl)nicotinic acid

Product 1

HCID 57377694HCID 57377694, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-(4-(1-(2-fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)-1H-imidazol-1-yl)nicotinic acid (74 mg, 0.203 mmol) in DMF (3 mL) was added CDI (40 mg, 0.244 mmol) and the resulting mixture stirred at 60° C. for 1 h. After cooling to room temperature ammonium hydroxide (320 μL, 2.03 mmol) was added and reaction mixture was stirred for 30 min and then evaporated. Purification by chromatography (reverse phase HPLC) afforded the title compound (58 mg, 74%) as a white solid. MS: m/e=364.1 [M+H]+.

Workup

  1. additionwas added
  2. customreaction mixture
  3. stirringwas stirred for 30 min
  4. customevaporated
  5. customPurification by chromatography (reverse phase HPLC)

Sources & evidence

ORD record
ord-0bfa86572878418fa57c2782cb617027
Source dataset
uspto-grants-2013_06
Patent number
US08466181B2

Reaction notes

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