HCID 178480998, compound → HCID 178480999, compound

HRID 897484Notes

Reaction equation

HRID 897484 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:26]3[CH2:31][CH2:30][C@@H:29]([N:32]4[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]4)[CH2:28][CH2:27]3)[N:9]=[C:10]([C:11]3[CH:25]=[CH:24][C:14]([O:15][C:16]4[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=4)=[CH:13][CH:12]=3)[C:3]=12>CO.[OH-].[NH4+].O.[Ni]>[NH2:21][CH2:20][C:19]1[CH:18]=[CH:17][C:16]([O:15][C:14]2[CH:24]=[CH:25][C:11]([C:10]3[C:3]4[C:4](=[N:5][CH:6]=[N:7][C:2]=4[NH2:1])[N:8]([C@H:26]4[CH2:31][CH2:30][C@@H:29]([N:32]5[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]5)[CH2:28][CH2:27]4)[N:9]=3)=[CH:12][CH:13]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 1

HCID 178480998HCID 178480998, compound

Product 1

HCID 178480999HCID 178480999, compoundYield 745.8%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 14923Ammonium HydroxideSolvent

Procedure

Cis-4-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenoxy)benzonitrile (0.600 g, 0.00118 mol) was dissolved in a mixture of methanol (50 mL) and concentrated solution of ammonium hydroxide in water (3 mL), 50% slurry of Raney nickel in water (2 mL) was added and the resulting mixture was hydrogenated at atmospheric pressure for 18 hours. The reaction mixture was filtered through a Celite pad, concentrated under reduced pressure and the residue digested with dichloromethane (50 mL). The organic phase was dried with magnesium sulfate, concentrated under reduced pressure and the residue suspended in diethyl ether (25 mL). The precipitate was collected by filtration and dried to yield cis-3-{4-[4-(aminomethyl)phenoxy]phenyl}-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.45 g, 0.0088 mol).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through a Celite pad
  3. concentrationconcentrated under reduced pressure
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-a8ee8f35d3904110a88ea70aeeb5f067
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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