Ammonium Hydroxide → 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide

HRID 1253538Notes

Reaction equation

HRID 1253538 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[C:18]([OH:20])=O)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1.C(N1C=CN=C1)([N:23]1C=CN=C1)=O.[OH-].[NH4+]>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[C:18]([NH2:23])=[O:20])[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 584048684-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid

Product 1

HCID 584046574-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid (14.0 mg, 0.051 mmol) and 1,1′-carbonyldiimidazole (13.0 mg, 0.077 mmol) in N,N-dimethylformamide (2 ml) was added 28% ammonium hydroxide solution (0.072 ml, 0.51 mmol). After 30 minutes the reaction mixture was purified directly by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% TFA to give 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide as gray solids. 1H NMR (500 MHz, DMSO-d6) δ 8.73 (s, 1H); 8.33 (s, 1H); 8.25 (s, 1H); 8.06 (s, 1H); 7.61 (s, 1H); 7.29 (s, 1H); 7.15 (s, 1H); 4.07 (s, 3H); 3.87 (s, 3H). LRMS (ESI) calculated for C13K4N5O2 [M+H]−, 272.1 found 272.0.

Workup

  1. customAfter 30 minutes the reaction mixture was purified directly by preparative HPLC Reverse phase (C-18)
  2. washeluting with acetonitrile/water+0.05% TFA

Sources & evidence

ORD record
ord-2923ad059bff4a60bfe183dbdbfb544a
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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