Ammonia → 2-(4-(3-(5-acetamido-2',4'-difluoro-[1,1'-biphenyl]-3-yl)-3H-imidazo[4,5-b]pyridin-6-yl)-1H-1,2,3-triazol-1-yl) acetamide

HRID 64159Notes

Reaction equation

HRID 64159 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([N:19]2[C:23]3=[N:24][CH:25]=[C:26]([C:28]4[N:29]=[N:30][N:31]([CH2:33][C:34](OCC)=[O:35])[CH:32]=4)[CH:27]=[C:22]3[N:21]=[CH:20]2)[CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[CH:10]=1)(=[O:3])[CH3:2].[NH3:39]>CO>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([N:19]2[C:23]3=[N:24][CH:25]=[C:26]([C:28]4[N:29]=[N:30][N:31]([CH2:33][C:34]([NH2:39])=[O:35])[CH:32]=4)[CH:27]=[C:22]3[N:21]=[CH:20]2)[CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 117777679HCID 117777679, compound

Product 1

HCID 1177776092-(4-(3-(5-acetamido-2',4'-difluoro-[1,1'-biphenyl]-3-yl)-3H-imidazo[4,5-b]pyridin-6-yl)-1H-1,2,3-triazol-1-yl) acetamideYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of the compound of Example 270 (100 mg, 0.19 mmol) in methanol was added methonalic ammonia at 0° C. and the mixture was stirred at RT for 16 h. The mixture was distilled completely and the crude product was purified by preparative HPLC to give the product in 13% yield (12 mg). δ 10.5 (s, 1H) 9.14-8.97 (d, 2H), 8.82 (s, 1H), 8.76 (d, 1H), 8.35 (s, 1H), 7.89 (d, 1H), 7.81-7.80 (m, 2H), 7.65-7.55 (m, 1H), 7.27 (m, 1H), 5.55 (s, 2H), 2.8 (s, 2H), 2.10 (s, 3H); LC-MS (ESI): Calculated mass: 515.5; Observed mass: 516.5 [M+H]+ (rt: 1.37 min).

Workup

  1. distillationThe mixture was distilled completely
  2. customthe crude product was purified by preparative HPLC
  3. customto give the product in 13% yield (12 mg)
  4. custom516.5 [M+H]+ (rt: 1.37 min)

Sources & evidence

ORD record
ord-7fb44b4196644894852f6baff7578f0b
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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