HCID 178476571, compound → HCID 178476557, compound

HRID 897868Notes

Reaction equation

HRID 897868 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].C[O:10][C:11]1[C:16]([CH2:17][NH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[C:33]4[C:28](=[N:29][CH:30]=[N:31][C:32]=4[NH2:34])[N:27]([C@H:35]4[CH2:40][CH2:39][C@H:38]([N:41]5[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]5)[CH2:37][CH2:36]4)[N:26]=3)=[CH:21][CH:20]=2)=[CH:15][CH:14]=[CH:13][N:12]=1>Br.C(O)(=O)C>[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[NH2:34][C:32]1[N:31]=[CH:30][N:29]=[C:28]2[N:27]([C@H:35]3[CH2:40][CH2:39][C@H:38]([N:41]4[CH2:42][CH2:43][N:44]([CH3:47])[CH2:45][CH2:46]4)[CH2:37][CH2:36]3)[N:26]=[C:25]([C:22]3[CH:21]=[CH:20][C:19]([NH:18][CH2:17][C:16]4[C:11](=[O:10])[NH:12][CH:13]=[CH:14][CH:15]=4)=[CH:24][CH:23]=3)[C:33]=12

Participants

4

Reactant 1

HCID 178476571HCID 178476571, compound

Product 1

HCID 178476557HCID 178476557, compoundYield 16.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

Trans-3-(4-[(2-methoxy-3-pyridyl)methyl]aminophenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine diacetate (0.105 g, 0.000199 mol) was dissolved in 30% hydrogen bromide in acetic acid (4 mL) and the mixture was refluxed for 1.5 hours. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield trans-3-[(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}anilino)methyl]-1,2-dihydro-2-pyridinone diacetate (0.0204 g, 0.0000324 mol) as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min)

Sources & evidence

ORD record
ord-98357002f512490394d02f374392e87d
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

Loading…