2-Methoxyethylamine → HCID 11420422, compound

HRID 2105205Notes

Reaction equation

HRID 2105205 reaction equation
CO[C:3]([C:5]1[N:10]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:17]=2)[N:8]=[C:7]([NH:27][C:28]2[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=2)[CH:6]=1)=[O:4].[CH3:34][O:35][CH2:36][CH2:37][NH2:38]>>[CH3:34][O:35][CH2:36][CH2:37][NH:38][C:3]([C:5]1[N:10]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:17]=2)[N:8]=[C:7]([NH:27][C:28]2[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=2)[CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 113053826-Methoxycarbonyl-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine

Product 1

HCID 11420422HCID 11420422, compoundYield 36%

Procedure

A mixture of 6-methoxycarbonyl-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine (Example 56) (200 mg, 0.45 mmol) and 2-methoxyethylamine (5 ml, 57.2 mmol) was heated at reflux for 18 hours. The reaction mixture was evaporated, the residue dissolved in methanol 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 and the residue was purified by chromatography on silica gel eluting with DCM/methanol (100:0 increasing in polarity to 90:10). The purified product was triturated with diethylether and the resulting solid collected by filtration to give the title compound (78 mg, 36%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customThe reaction mixture was evaporated
  4. dissolutionthe residue dissolved in methanol
  5. washThe column was eluted with methanol
  6. washto elute any neutrals
  7. washto elute the product
  8. customThe solvent was removed by evaporation
  9. customthe residue was purified by chromatography on silica gel eluting with DCM/methanol (100:0 increasing in polarity to 90:10)
  10. customThe purified product was triturated with diethylether
  11. filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record
ord-7209c57a4fb14b27bfb4e322b937598c
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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