Potassium Carbonate → HCID 58109443, compound

HRID 2037596Notes

Reaction equation

HRID 2037596 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)[O:14][C:13](=[O:15])[N:12]([C@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[CH:19]=2)[CH3:17])[CH2:11][CH2:10]1)(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH3:38][S:39]([NH2:42])(=[O:41])=[O:40]>C(#N)C>[Br:24][C:20]1[CH:19]=[C:18]([C@@H:16]([N:12]2[CH2:11][CH2:10][C@:9]([CH2:8][CH2:7][CH2:6][NH:42][S:39]([CH3:38])(=[O:41])=[O:40])([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[O:14][C:13]2=[O:15])[CH3:17])[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 72879MethanesulfonamideHCID 58109118HCID 58109118, compound

Product 1

HCID 58109443HCID 58109443, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-((R)-3-((S)-1-(3-bromophenyl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propyl methanesulfonate (6.8 mg, 0.013 mmol) was diluted with acetonitrile (2 mL), added K2CO3 (10 mg, excess) and methanesulfonamide (2.5 mg, 2 equiv.). The mixture was stirred overnight at rt. After filtration and concentration, the residue was purified by preparative HPLC to afford N-(3-((R)-3-((S)-1-(3-bromophenyl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propyl)methanesulfonamide (2.5 mg, 37%). LC-MS (3 min) tR=1.87 min, m/z=514, 516 (M+1). 1H NMR (CDCl3) 7.31 (m, 1H), 7.23 (m, 2H), 7.14-7.05 (m, 3H), 7.02 (t, 1H), 6.87 (d, 1H), 5.64 (q, 1H), 4.17 (m, 2H), 2.97 (s, 3H), 2.33-2.11 (m, 3H), 1.52 (d, 3H).

Workup

  1. filtrationAfter filtration and concentration
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-8dca45c76a1d4be99ef01a4db879fb03
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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