Triethylamine → HCID 59627236, compound

HRID 1523253Notes

Reaction equation

HRID 1523253 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([CH2:16][CH2:17][CH2:18][OH:19])[NH:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl>[CH3:35][S:36]([O:19][CH2:18][CH2:17][CH2:16][C@:13]1([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[CH2:14][CH2:15][N:10]([C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH3:9])[C:11](=[O:27])[NH:12]1)(=[O:38])=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59627203HCID 59627203, compound

Product 1

HCID 59627236HCID 59627236, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)-4-(3-hydroxypropyl)tetrahydropyrimidin-2(1H)-one (50 mg, 0.12 mmol) and triethylamine (161 mg, 1.59 mmol) in CH2Cl2 (5 mL) was added methanesulfonyl chloride (91 mg, 0.8 mmol) at 0° C., and the reaction mixture was stirred at rt till the reaction was over. The reaction was quenched with H2O, and the mixture was extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to give crude 3-((R)-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)-2-oxohexahydropyrimidin-4-yl)propyl methanesulfonate (58 mg, 95%), which was used for the next step without further purification.

Workup

  1. customThe reaction was quenched with H2O
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cbff5c77b238409fa2340d87ce5af3c6
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

Loading…