Benzoyl chloride → (2S)-2-Methyl-7-(morpholin-4-yl)-1-(phenylcarbonyl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

HRID 72380Notes

Reaction equation

HRID 72380 reaction equation
[H-].[Na+].[CH3:3][C@@:4]1([C:20]([F:23])([F:22])[F:21])[CH2:19][N:7]2[C:8](=[O:18])[CH:9]=[C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:11]=[C:6]2[NH:5]1.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:3][C@@:4]1([C:20]([F:23])([F:21])[F:22])[CH2:19][N:7]2[C:8](=[O:18])[CH:9]=[C:10]([N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[N:11]=[C:6]2[N:5]1[C:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:31]

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 136069602(2S)-2-methyl-7-morpholin-4-yl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

Product 1

HCID 50899528(2S)-2-Methyl-7-(morpholin-4-yl)-1-(phenylcarbonyl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

14.2 mg of sodium hydride are added to a solution of 150 mg of (2S)-2-methyl-7-morpholin-4-yl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]-pyrimidin-5-one (Example 1j), in 3 ml of tetrahydrofuran. After stirring for 25 minutes at a temperature in the region of 20° C., 0.092 ml of benzoyl chloride is added. The reaction medium is stirred for 1 hour at ambient temperature before the addition of 1.5 ml of a saturated solution of sodium bicarbonate and ethyl acetate. The organic phase is successively separated, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate, filtered, and then concentrated under reduced pressure. After purification by silica column chromatography (eluent: dichloromethane/methanol: 98/02), 49 mg of (2S)-2-methyl-7-(morpholin-4-yl)-1-(phenylcarbonyl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)one are obtained in the form of a brown solid, the characteristics of which are the following:

Workup

  1. additionis added
  2. customThe organic phase is successively separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customAfter purification by silica column chromatography (eluent: dichloromethane/methanol: 98/02), 49 mg of (2S)-2-methyl-7-(morpholin-4-yl)-1-(phenylcarbonyl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)one
  8. customare obtained in the form of a brown solid

Sources & evidence

ORD record
ord-fe60d28c4b8f467ba934e00822afdd25
Source dataset
uspto-grants-2014_09
Patent number
US08828997B2

Reaction notes

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