HCID 178480682, compound → HCID 178480683, compound

HRID 1048807Notes

Reaction equation

HRID 1048807 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][C:11]2[CH:12]=[C:13]3[C:19]([NH:20][C:21](=[O:42])[C:22]4[CH:27]=[CH:26][C:25]([N:28]5[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]5)=[CH:24][C:23]=4[NH:35][CH:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)=[N:18][NH:17][C:14]3=[N:15][CH:16]=2)[CH:5]=[C:6]([F:8])[CH:7]=1>O1CCCC1.CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[CH2:9][CH2:10][C:11]1[CH:12]=[C:13]2[C:19]([NH:20][C:21](=[O:42])[C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)=[CH:24][C:23]=3[NH:35][CH:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)=[N:18][NH:17][C:14]2=[N:15][CH:16]=1

Participants

5

Reactant 1

HCID 178480682HCID 178480682, compound

Product 1

HCID 178480683HCID 178480683, compoundYield 61.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10 mg of 10% Pd/C is added to 100 mg (0.175 mmol) of N-(5-((3,5-difluorophenyl)ethynyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)-2-(tetrahydro-2H-pyran-4-ylamino)benzamide in solution in a mixture of 10 ml of tetrahydrofuran and 5 ml of methanol before placing the reaction medium under an atmosphere of hydrogen. The reaction mixture is stirred for 12 hours at room temperature and then filtered on Celite and concentrated. 62 mg (yield=60%) of N-(5-(3,5-difluorophenethyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)-2-(tetrahydro-2H-pyran-4-ylamino)benzamide are isolated in the form of a white solid. LCMS (EI, m/z): (M+1) 576.23.

Workup

  1. filtrationfiltered on Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-193452ae43fd419dafd9ebc9bd347e45
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Reaction notes

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