Lithium Hydroxide → 3-[3-(2-Chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]aniline

HRID 1159967Notes

Reaction equation

HRID 1159967 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]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=23)[CH:5]=[CH:4][N:3]=1.[Li+].[OH-].C([O-])(O)=O.[Na+]>C1COCC1.O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=3)[NH2:24])=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=23)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 516892Sodium BicarbonateHCID 86618783N-{3-[3-(2-chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide

Product 1

HCID 595114323-[3-(2-Chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]anilineYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the solution of N-{3-[3-(2-chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide (0.40 g) in THF (27 mL) and water (3 mL) was added 5% LiOH solution (2.3 mL). The reaction was kept stirring at rt for 15 h and was worked up with sat. NaHCO3 solution (20 mL) and extracted with EtOAc (2×20 mL). The organic phase was dried (Na2SO4) and concentrated to afford the crude 3-[3-(2-chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]aniline (0.30 g, 95% yield) as yellow solid. ES-LC/MS (M+H)+=340.

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1a68a08a62924e6094dac113f996773d
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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