Acetonitrile → Methyl[4-({[3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9h-purin-9-yl)propyl][(4-methylpiperazin-1-yl)acetyl]amino}methyl)phenyl]acetate

HRID 1095329Notes

Reaction equation

HRID 1095329 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][N:16]2[C:24](=[O:25])[NH:23][C:22]3[C:17]2=[N:18][C:19]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[N:20][C:21]=3[NH2:26])=[CH:7][CH:6]=1.Cl[CH2:34][C:35](Cl)=[O:36].[CH3:38][C:39]#[N:40]>>[CH3:1][O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]([CH2:13][CH2:14][CH2:15][N:16]2[C:24](=[O:25])[NH:23][C:22]3[C:17]2=[N:18][C:19]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[N:20][C:21]=3[NH2:26])[C:35](=[O:36])[CH2:34][N:40]2[CH2:8][CH2:11][N:12]([CH3:13])[CH2:38][CH2:39]2)=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 6577Chloroacetyl chlorideHCID 90697362Methyl[4-({[3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)propyl]amino}methyl)phenyl]acetate

Product 1

HCID 23649460Methyl[4-({[3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9h-purin-9-yl)propyl][(4-methylpiperazin-1-yl)acetyl]amino}methyl)phenyl]acetate

Procedure

The product from step (ix) (200 mg) was suspended in MeCN. Chloroacetyl chloride (0.02 ml) added and the mixture stirred at rt for 4 h. The mixture was concentrated under reduced pressure, piperazine (0.02 ml) in DMSO (1 ml) was added and the mixture heated at 60° C. for 24 h. The mixture was purified by RPHPLC. Yield 80 mg.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure, piperazine (0.02 ml) in DMSO (1 ml)
  2. additionwas added
  3. temperaturethe mixture heated at 60° C. for 24 h
  4. customThe mixture was purified by RPHPLC

Sources & evidence

ORD record
ord-03f4b6d868cd40f4a3fd4ba996801ea4
Source dataset
uspto-grants-2012_03
Patent number
US08138172B2

Reaction notes

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