Tributylamine → N-[4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-N-(methylsulfonyl)methanesulfonamide

HRID 1479790Notes

Reaction equation

HRID 1479790 reaction equation
[CH3:1][C:2]1([CH3:22])[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[CH:10][C:11]([N:13]([S:18]([CH3:21])(=[O:20])=[O:19])[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][C:4]=2[O:3]1.[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(N(CCCC)CCCC)CCC>CN(C)C1C=CN=CC=1.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CS(C)=O>[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:6]2[C:5]3[CH:9]=[CH:10][C:11]([N:13]([S:18]([CH3:21])(=[O:19])=[O:20])[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][C:4]=3[O:3][C:2]([CH3:22])([CH3:1])[C:7]2=[O:8])=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 7622TributylamineHCID 2856454-Fluorophenylboronic acidHCID 73297136N-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-N-(methylsulfonyl)methanesulfonamide

Product 1

HCID 73294711N-[4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-N-(methylsulfonyl)methanesulfonamideYield 95.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 165397Cupric acetate monohydrateCatalystHCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
20 °C

Procedure

N-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-N-(methylsulfonyl)methanesulfonamide (7.50 g), 4-fluorophenylboronic acid (5.27 g), 4-dimethylaminopyridine (0.53 g), tributylamine (3.20 g) and copper(II) acetate monohydrate (0.43 g) were added to dimethylsulfoxide (56 mL), and the mixture was stirred at 20° C. for 26 hours under blowing air (7 to 10 mL/min) thereto. The reaction mixture was added dropwise to a mixed solution of dimethylsulfoxide/concentrated hydrochloric acid/water (19 mL/4.5 g/34 mL) at about 15° C., and washed with dimethylsulfoxide (7.5 mL). The mixture was stirred at 10° C. for 3 hours, then the precipitated crystals were successively washed with dimethylsulfoxide/water (12 mL/3 mL) and water (75 mL), and then dried to obtain the title compound (9.09 g) as white crystals (yield: 95%, purity: 92%).

Workup

  1. washwashed with dimethylsulfoxide (7.5 mL)
  2. stirringThe mixture was stirred at 10° C. for 3 hours
  3. washthe precipitated crystals were successively washed with dimethylsulfoxide/water (12 mL/3 mL) and water (75 mL)
  4. customdried

Sources & evidence

ORD record
ord-635a53138b8046cba79a9b445d7e86bb
Source dataset
uspto-grants-2016_08
Patent number
US09409874B2

Reaction notes

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