1-Methylpiperazine → HCID 59577358, compound

HRID 1773419Notes

Reaction equation

HRID 1773419 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([F:35])[CH:34]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16]([C:18]1[C:23]([NH:24][CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:22][C:21](F)=[CH:20][N:19]=1)=[O:17].[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>CCOC(C)=O>[F:35][C:33]1[CH:32]=[C:4]([CH:3]=[C:2]([F:1])[CH:34]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16]([C:18]1[C:23]([NH:24][CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:22][C:21]([N:40]2[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]2)=[CH:20][N:19]=1)=[O:17]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 68672100HCID 68672100, compound

Product 1

HCID 59577358HCID 59577358, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-5-fluoro-3-(tetrahydro-2H-pyran-4-ylamino)pyridine-2-carboxamide (925 mg, 1.92 mmol) and N-methylpiperazine (20 mL) was stirred at 60° C. for 48 hours. The reaction mixture was then diluted with EtOAc and washed with NaHCO3 sat.sol. The organic layer was dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography on silica gel using DCM/EtOH/NH3 5N in MeOH 100:5:0.5 as the eluant, affording 600 mg of the title compound.

Workup

  1. washwashed with NaHCO3 sat.sol
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9530b78c562e46b7ac9b16791a641cde
Source dataset
uspto-grants-2016_02
Patent number
US09255087B2

Reaction notes

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