Potassium Carbonate → HCID 59627213, compound

HRID 1523254Notes

Reaction equation

HRID 1523254 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C@:9]1([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:14][CH2:13][N:12]([C@H:15]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)[CH3:16])[C:11](=[O:24])[NH:10]1)(=O)=O.[CH3:32][S:33]([NH2:36])(=[O:35])=[O:34].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([C@@H:15]([N:12]2[CH2:13][CH2:14][C@:9]([CH2:8][CH2:7][CH2:6][NH:36][S:33]([CH3:32])(=[O:35])=[O:34])([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[NH:10][C:11]2=[O:24])[CH3:16])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 72879MethanesulfonamideHCID 59627236HCID 59627236, compound

Product 1

HCID 59627213HCID 59627213, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-((R)-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)-2-oxohexa hydropyrimidin-4-yl)propyl methanesulfonate (58 mg, 0.11 mmol) and methanesulfonamide (105 mg, 1.10 mmol) in acetone (10 mL) was added K2CO3 (31 mg, 0.22 mmol), and the mixture was refluxed overnight. The reaction was quenched with water, and the mixture was extracted with EtOAc. After removal of the solvent, the mixture was extracted with EtOAc, and the organic solution was washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by preparative TLC and preparative HPLC to give N-(3-((R)-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)-2-oxohexahydropyrimidin-4-yl)propyl)methanesulfonamide (8 mg, 14%). 1H NMR (CDCl3): 1.18□m, 1H), 1.45 (d, 3H), 1.50 (m, 1H), 1.88-2.16 (m, 5H), 2.84 (m, 4H), 3.02 (m, 2H), 4.70 (s, 1H), 5.63 (m, 1H), 6.88-6.98 (m, 4H), 7.12 (m, 2H), 7.30 (m, 2H). LC-MS Method 1 tR=1.146 min, m/z=512.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe reaction was quenched with water
  3. extractionthe mixture was extracted with EtOAc
  4. customAfter removal of the solvent
  5. extractionthe mixture was extracted with EtOAc
  6. washthe organic solution was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give the crude product, which
  11. customwas purified by preparative TLC and preparative HPLC

Sources & evidence

ORD record
ord-b5d88c1e3e674be3a4f555c5dcd923ae
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

Loading…