HCID 178476433, compound → HCID 178476508, compound

HRID 897794Notes

Reaction equation

HRID 897794 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].C([O:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:27]4[C:22](=[N:23][CH:24]=[N:25][C:26]=4[NH2:28])[N:21]([C@H:29]4[CH2:34][CH2:33][C@H:32]([N:35]5[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]5)[CH2:31][CH2:30]4)[N:20]=3)=[CH:15][CH:14]=2)[N:11]=[CH:10][CH:9]=1)C>Br.C(O)(=O)C>[C:1]([OH:4])(=[O:3])[CH3:2].[C:1]([OH:4])(=[O:3])[CH3:2].[NH2:28][C:26]1[N:25]=[CH:24][N:23]=[C:22]2[N:21]([C@H:29]3[CH2:30][CH2:31][C@H:32]([N:35]4[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]4)[CH2:33][CH2:34]3)[N:20]=[C:19]([C:16]3[CH:15]=[CH:14][C:13]([N:12]4[C:8](=[O:7])[CH2:9][C:10]([CH3:1])=[N:11]4)=[CH:18][CH:17]=3)[C:27]=12

Participants

4

Reactant 1

HCID 178476433HCID 178476433, compound

Product 1

HCID 178476508HCID 178476508, compoundYield 170.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of trans-3-[4-(5-ethoxy-1H-1-pyrazolyl)phenyl]-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine acetate (0.100 g, 0.000194 mol) in 30% hydrobromic acid in acetic acid (2.5 mL) was heated at reflux for 1.5 hours. The reaction mixture was concentrated under reduced pressure and the residue neutralized with concentrated solution of ammonium hydroxide in water. The resulting suspension was concentrated under reduced pressure and the residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 5-45% acetonitrile-0.1M ammonium acetate over 20 min, 21 mL/min) to yield trans-1-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-3-methyl-4,5-dihydro-1H-5-pyrazolone diacetate (0.066 g, 0.00011 mol) as a white solid.

Workup

  1. temperatureat reflux for 1.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. concentrationThe resulting suspension was concentrated under reduced pressure
  4. customthe residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 5-45% acetonitrile-0.1M ammonium acetate over 20 min, 21 mL/min)

Sources & evidence

ORD record
ord-9cc75f8886954f9f8fdc750fe305b883
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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