Methylamine → HCID 18545328, compound

HRID 564876Notes

Reaction equation

HRID 564876 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]([CH3:13])=[C:11](/[CH:14]=[CH:15]/[CH2:16][N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=4)[CH2:19][CH2:18]3)[CH:10]=[N:9]2)[CH:5]=[C:4]([Cl:31])[N:3]=1.[CH3:32][NH2:33]>C(O)C>[ClH:31].[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]([CH3:13])=[C:11](/[CH:14]=[CH:15]/[CH2:16][N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=4)[CH2:19][CH2:18]3)[CH:10]=[N:9]2)[CH:5]=[C:4]([NH:33][CH3:32])[N:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 18520580HCID 18520580, compound

Product 1

HCID 18545328HCID 18545328, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture consisting of 300 mg of 1-[1-(2-amino-6-chloro-4-pyrimidinyl)-5-methyl-4-pyrazolyl]-3-[4-(3,5-difluorophenyl)-1-piperazinyl]-1-trans-propene, 10.2 ml of a 40% methylamine aqueous solution, and 15 ml of ethanol was stirred at 60° C. for 4.5 hours. The reaction mixture was concentrated, and a saturated sodium hydrogencarbonate aqueous solution was added to the residue. The mixture was extracted three times with chloroform. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was removed by evaporation, and the residue was subjected to silica gel column chromatography using a 19:1 mixture of chloroform and methanol as a developing solvent. The fraction containing the desired product was concentrated, and a 1N ethanolic solution of hydrochloric acid was added to the residue. Concentration followed by recrystallization from ethanol gave 95 mg of the title compound as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiona saturated sodium hydrogencarbonate aqueous solution was added to the residue
  3. extractionThe mixture was extracted three times with chloroform
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by evaporation
  7. additiona 19:1 mixture of chloroform and methanol as a developing solvent
  8. additionThe fraction containing the desired product
  9. concentrationwas concentrated
  10. additiona 1N ethanolic solution of hydrochloric acid was added to the residue
  11. concentrationConcentration
  12. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-4b350067c4d045f09b8533f770a961d6
Source dataset
uspto-grants-2001_01
Patent number
US06169086A

Reaction notes

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