Methanol → HCID 58056244, compound

HRID 1773612Notes

Reaction equation

HRID 1773612 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:20]2[CH2:24][CH2:23][CH:22]([NH:25]C(=O)C(F)(F)F)[CH2:21]2)=[C:6]([NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]=23)=[O:10])[CH:7]=1.CO.[OH-].[Na+]>C(OCC)(=O)C>[NH2:25][CH:22]1[CH2:23][CH2:24][N:20]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=2[NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]=23)=[O:10])[CH2:21]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86661374HCID 86661374, compound

Product 1

HCID 58056244HCID 58056244, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid {5-chloro-2-[3-(2,2,2-trifluoro-acetylamino)-pyrrolidin-1-yl]-phenyl}-amide (50 mg), methanol (2 mL) and an aqueous solution of sodium hydroxide (4 M, 1 mL) was heated at 60° C. for 1 hour. The resulting mixture was cooled, diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 30 mg of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [2-(3-amino-pyrrolidin-1-yl)-5-chloro-phenyl]-amide (light yellow foam) without further purifications. MS=356 [M]+.

Workup

  1. temperatureThe resulting mixture was cooled
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-99e81306803d4aef9d536d4ceac883d6
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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