HCID 178476433, compound → HCID 178476508, compound

HRID 432505Notes

Reaction equation

HRID 432505 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-7c95a82369f7485da4ef253f9d7fb4ea
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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