Dimethylformamide → HCID 178476561, compound

HRID 897617Notes

Reaction equation

HRID 897617 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([C@H:18]3[CH2:23][CH2:22][C@@H:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)[N:9]=2)=[CH:4][CH:3]=1.Br[CH2:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34].C(N(CC)C(C)C)(C)C.CN(C)C=[O:53]>>[C:33]([OH:53])(=[O:34])[CH3:35].[C:33]([OH:53])(=[O:34])[CH3:35].[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:10]([C@H:18]3[CH2:23][CH2:22][C@@H:21]([N:24]4[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]4)[CH2:20][CH2:19]3)[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][CH2:32][C:33]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[O:34])=[CH:7][CH:6]=3)[C:16]=12

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6259Phenacyl bromideHCID 81531DiisopropylethylamineHCID 178480983HCID 178480983, compound

Product 1

HCID 178476561HCID 178476561, compound

Procedure

Cis-3-(4-aminophenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.6 g, 0.00148 mol) and bromoacetophenone (0.295 g, 0.00148 mol) were dissolved in anhydrous N,N-dimethylformamide (30 mL) and the resulting mixture was stirred at ambient temperature under an atmosphere of nitrogen for 5 min. N,N-diisopropylethylamine (0.095 g, 0.00074 mol) was added dropwise and stirring under an atmosphere of nitrogen was continued for sixteen hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1 M ammonium acetate over 25 min, 21 mL/min) to yield cis-2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}anilino)-1-phenyl-1-ethanone diacetate (0.410 g, 0.00064 mol) as a white solid.

Workup

  1. stirringstirring under an atmosphere of nitrogen
  2. waitwas continued for sixteen hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1 M ammonium acetate over 25 min, 21 mL/min)

Sources & evidence

ORD record
ord-515169a44a6c4b01bb8cfa1b8f3a1528
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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