Acetic Acid → HCID 178481001, compound

HRID 432193Notes

Reaction equation

HRID 432193 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(C#N)=[CH:18][CH:17]=4)=[CH:13][CH:12]=3)[C:3]=12.[C:39]([OH:42])(=[O:41])[CH3:40]>Cl.O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:26]3[CH2:27][CH2:28][C@@H:29]([N:32]4[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]4)[CH2:30][CH2:31]3)[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:15][C:16]4[CH:23]=[CH:22][C:40]([C:39]([OH:42])=[O:41])=[CH:18][CH:17]=4)=[CH:24][CH:25]=3)[C:3]=12

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 178480998HCID 178480998, compound

Product 1

HCID 178481001HCID 178481001, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Cis-4-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenoxy)benzonitrile (0.200 g, 0.000394 mol) was dissolved in a mxture of acetic acid (15 mL) and 6N solution of hydrochloric acid in water (15 mL) and the solution was heated at reflux for 12 hours. It was cooled to ambient temperature and concentrated under reduced pressure and the residue recrystallized from N,N-dimethylformamide to yield cis-4-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenoxy)benzoic acid (0.100 g, 0.00019 mol) as an off-white solid.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 12 hours
  3. concentrationconcentrated under reduced pressure
  4. customthe residue recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-c91840afe626430abdb07997572a488b
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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