Acetic Anhydride → HCID 178474556, compound

HRID 432195Notes

Reaction equation

HRID 432195 reaction equation
[NH2:1][CH2:2][C:3]1[CH:38]=[CH:37][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:22]4[C:17](=[N:18][CH:19]=[N:20][C:21]=4[NH2:23])[N:16]([C@H:24]4[CH2:29][CH2:28][C@@H:27]([N:30]5[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]5)[CH2:26][CH2:25]4)[N:15]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[C:39]([O:42]C(=O)C)(=[O:41])[CH3:40]>N1C=CC=CC=1>[C:39]([OH:42])(=[O:41])[CH3:40].[NH2:23][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:16]([C@H:24]3[CH2:29][CH2:28][C@@H:27]([N:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)[CH2:26][CH2:25]3)[N:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([O:7][C:6]4[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:39](=[O:41])[CH3:40])=[CH:38][CH:37]=4)=[CH:9][CH:10]=3)[C:22]=12

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178480999HCID 178480999, compound

Product 1

HCID 178474556HCID 178474556, compoundYield 149.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cis-3-{4-[4-(aminomethyl)phenoxy]phenyl}-1-[4-(4-methylpiperazino) cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.051 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-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenoxy)benzyl]acetamide acetate (0.046 g, 0.0000749 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-6f49a85161e7461983cc6e2b06aedcf0
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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