beta-BUTYROLACTONE → HCID 178476462, compound

HRID 897479

Reaction equation

HRID 897479 reaction equation
[NH2:1][CH:2]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[N:15][C:16]=3[NH2:18])[N:11]([C@H:19]3[CH2:24][CH2:23][C@@H:22]([N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)[CH2:21][CH2:20]3)[N:10]=2)=[CH:5][CH:4]=1.[C:38]1(=[O:43])[O:42][CH:40]([CH3:41])[CH2:39]1>O1CCOCC1>[C:38]([OH:43])(=[O:42])[CH3:39].[NH2:18][C:16]1[N:15]=[CH:14][N:13]=[C:12]2[N:11]([C@H:19]3[CH2:24][CH2:23][C@@H:22]([N:25]4[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]4)[CH2:21][CH2:20]3)[N:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH:2]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[NH:1][C:38](=[O:43])[CH2:39][CH:40]([OH:42])[CH3:41])=[CH:8][CH:7]=3)[C:17]=12

Participants

4

Reactant 2

HCID 18303beta-BUTYROLACTONEHCID 178480954HCID 178480954, compound

Product 1

HCID 178476462HCID 178476462, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Cis-3-{4-[amino(phenyl)methyl]phenyl}-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.05 g, 0.0001 mol) and β-butyrolactone (0.009 g, 0.0001 mol) were heated in dioxane at reflux for three hours. The solvent was removed under reduced pressure and the resulting residue 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 cis-N1-[(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)(phenyl)methyl]-3-hydroxybutanamide acetate (0.027 g, 0.000042 mol) as a white solid.

Workup

  1. temperatureat reflux for three hours
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting residue 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-dffb5dc1740a46fe82ee92918c63df4c
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Linked notes

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