Ethanol → HCID 136375761, compound

HRID 869263Notes

Reaction equation

HRID 869263 reaction equation
[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]1[N:15]=[C:16](SC)[NH:17][C:18](=[O:23])[C:19]=1[C:20]([NH2:22])=[O:21])(=[O:6])=[O:5])([CH3:3])[CH3:2].[NH2:26][CH2:27][C:28]1([N:34]([CH3:36])[CH3:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.CN1C(=O)CCC1.C(O)C>C(OCC)(=O)C.O>[CH3:35][N:34]([CH3:36])[C:28]1([CH2:27][NH:26][C:16]2[NH:17][C:18](=[O:23])[C:19]([C:20]([NH2:22])=[O:21])=[C:14]([NH:13][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])[N:15]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 702EthanolHCID 13387N-methyl-2-pyrrolidoneHCID 21134031-(Aminomethyl)-N,N-dimethylcyclohexan-1-amineHCID 136375769HCID 136375769, compound

Product 1

HCID 136375761HCID 136375761, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 4-{[2-(isopropylsulfonyl)phenyl]amino}-2-(methylsulfanyl)-6-oxo-1,6-dihydropyrimidine-5-carboxamide (Preparation Example 294) (200 mg), 1-(aminomethyl)-N,N-dimethylcyclohexylamine (409 mg) and NMP (1 mL) was heated at 180° C. for 10 minutes using a microwave reaction system. After cooling, the reaction liquid was diluted with ethyl acetate, and the precipitated crystal was collected by filtration and washed with ethyl acetate to give a white solid. To the white solid, a mixed solvent of ethanol and water was added, heated and then cooled, and the precipitated solid was collected by filtration to give 2-({[1-(dimethylamino)cyclohexyl]methyl}amino)-4-{[2-(isopropylsulfonyl)phenyl]amino}-6-oxo-1,6-dihydropyrimidine-5-carboxamide (136 mg) as a white solid.

Workup

  1. customa microwave reaction system
  2. temperatureAfter cooling
  3. customthe reaction liquid
  4. filtrationthe precipitated crystal was collected by filtration
  5. washwashed with ethyl acetate
  6. customto give a white solid
  7. temperatureheated
  8. temperaturecooled
  9. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-e484000b137e411483208c8c86e147f3
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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