Water → {3-[3-(2-Chloro-4-pyrimidinyl)-6-methylpyrazolo[1,5-a]pyridin-2-yl]phenyl}amine

HRID 1157648Notes

Reaction equation

HRID 1157648 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[CH:19]=[C:20]([NH:24]C(=O)C(F)(F)F)[CH:21]=[CH:22][CH:23]=3)=[N:10][N:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[Li+].[OH-].O>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=3)=[N:10][N:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57737199N-{3-[3-(2-Chloro-4-pyrimidinyl)-6-methylpyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide

Product 1

HCID 57737218{3-[3-(2-Chloro-4-pyrimidinyl)-6-methylpyrazolo[1,5-a]pyridin-2-yl]phenyl}amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-{3-[3-(2-Chloro-4-pyrimidinyl)-6-methylpyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide (1.70 g, 3.94 mmol) and LiOH (0.50 g, 11.8 mmol) were combined in THF (30 mL) and water (5 mL) and stirred at 40° C. for 3 h. The mixture was cooled, concentrated to remove the THF, and extracted with DCM. The organic phase was concentrated to afford {3-[3-(2-chloro-4-pyrimidinyl)-6-methylpyrazolo[1,5-a]pyridin-2-yl]phenyl}amine which was carried on crude to Step C. ES-LC/MS m/z=336 [M+H]+.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customto remove the THF
  4. extractionextracted with DCM
  5. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-ae4ac85b40f24199855b9947458883cc
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

Loading…