beta-BUTYROLACTONE → HCID 178476462, compound

HRID 432189

Reaction equation

HRID 432189 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-7d67f69d1a324c51b50e0c25bfda3a2d
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Linked notes

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