1-Methylpiperazine → HCID 11386498, compound

HRID 2105212Notes

Reaction equation

HRID 2105212 reaction equation
CC1C=CC(S(O[CH2:12][C:13]2[N:18]=[C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH:20]3[C:24]3[O:28][N:27]=[C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[CH:25]=3)[N:16]=[C:15]([NH:35][CH:36]3[CH:40]=[C:39]([CH3:41])[NH:38][N:37]3S(C3C=CC(C)=CC=3)(=O)=O)[CH:14]=2)(=O)=O)=CC=1.[CH3:52][N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1>>[CH3:52][N:53]1[CH2:58][CH2:57][N:56]([CH2:12][C:13]2[N:18]=[C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH:20]3[C:24]3[O:28][N:27]=[C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[CH:25]=3)[N:16]=[C:15]([NH:35][C:36]3[CH:40]=[C:39]([CH3:41])[NH:38][N:37]=3)[CH:14]=2)[CH2:55][CH2:54]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 86610854HCID 86610854, compound

Product 1

HCID 11386498HCID 11386498, compoundYield 72.5%

Procedure

A mixture of 6-[(4-methylphenylsulphonyloxy)methyl]-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-2-N-[4-methylphenylsulphonyl]-1H-pyrazol-3-ylamino)pyrimidine (Method 52) (214 mg, 0.295 mmol) and 1-methylpiperazine (3.0 ml, 27.1 mmol) was heated at reflux for 4 hours. The volatiles were removed by evaporation and the residue purified by reverse phase HPLC using a C18 column eluting with water/acetonitrile/TFA (95:5:0.2 decreasing in polarity to 0:100:0.2). Product containing fractions were combined and passed through a 50 g isolute SCX-2 ion exchange column. The column was eluted with methanol to elute any neutrals, followed by 7M methanolic ammonia to elute the product. The solvent was removed by evaporation of give the title compound (107 mg, 71%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe volatiles were removed by evaporation
  4. customthe residue purified by reverse phase HPLC
  5. washeluting with water/acetonitrile/TFA (95:5:0.2 decreasing in polarity to 0:100:0.2)
  6. additionProduct containing fractions
  7. washThe column was eluted with methanol
  8. washto elute any neutrals
  9. washto elute the product
  10. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-168fcc27fde9451bbcd4c7ed5e0b3cec
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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