Acetic Anhydride → HCID 178474524, compound

HRID 897478Notes

Reaction equation

HRID 897478 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]([O:41][C:42](=[O:44])[CH3:43])(=[O:40])[CH3:39]>N1C=CC=CC=1>[C:38]([OH:41])(=[O:40])[CH3:39].[C:38]([OH:41])(=[O:40])[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[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)[CH2:21][CH2:20]3)[N:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH:2]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[NH:1][C:42](=[O:44])[CH3:43])=[CH:4][CH:5]=3)[C:17]=12

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178480954HCID 178480954, compound

Product 1

HCID 178474524HCID 178474524, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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) was dissolved in anhydrous pyridine (1 mL), acetic anhydride (0.010 g, 0.0001 mol) was added and the resulting solution was stirred at ambient temperature for twenty 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]acetamide diacetate (0.015 g, 0.000021 mol) as a white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. 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-13f906b3ac6b4a46bd32c949345a4ad9
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

Loading…