Sodium methanethiolate → HCID 56646342, compound

HRID 1773613Notes

Reaction equation

HRID 1773613 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:6]([NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]3[CH:19]=[C:18]([O:20]C)[CH:17]=[N:16][C:15]=23)=[O:10])[CH:7]=1.C[S-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:6]([NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]3[CH:19]=[C:18]([OH:20])[CH:17]=[N:16][C:15]=23)=[O:10])[CH:7]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 58056210HCID 58056210, compound

Product 1

HCID 56646342HCID 56646342, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 6-methoxy-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (5-chloro-2-piperidin-1-yl-phenyl)-amide (100 mg) and sodium methanethiolate (45 mg) in N,N-dimethylformamide (ca. 2 mL) was heated in a sealed tube at 160° C. for 48 hours. The resulting mixture was evaporated under reduced pressure and the residue was dissolved in a mixture of chloroform and methanol, absorbed onto silica gel and purified by flash chromatography (DCM/MeOH/AcOH) to give 25.4 mg (26% yield) of 6-hydroxy-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (5-chloro-2-piperidin-1-yl-phenyl)-amide as a yellow solid. MS=372 [M+H]+; MP>300° C.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of chloroform and methanol
  3. customabsorbed onto silica gel
  4. custompurified by flash chromatography (DCM/MeOH/AcOH)

Sources & evidence

ORD record
ord-799d5b18e6f24c898a4378a67536add6
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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