Propylphosphonic anhydride → 4-chloro-N-[5-chloro-2-(8-fluoro-2,3-dihydro-benzo[1,4]oxazine-4-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide

HRID 419081Notes

Reaction equation

HRID 419081 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([C:33]([F:36])([F:35])[F:34])[CH:27]=2)(=[O:25])=[O:24])[C:16]([C:19](O)=[O:20])=[N:17][CH:18]=1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CCN(CC)CC>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([S:23]([NH:22][C:15]2[C:16]([C:19]([N:7]3[C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[C:11]=4[O:10][CH2:9][CH2:8]3)=[O:20])=[N:17][CH:18]=[C:13]([Cl:12])[CH:14]=2)(=[O:25])=[O:24])=[CH:27][C:28]=1[C:33]([F:34])([F:36])[F:35]

Participants

5

Reactant 3

HCID 111923Propylphosphonic anhydrideHCID 162444518-Fluoro-3,4-dihydro-2H-1,4-benzoxazineHCID 579420775-Chloro-3-(4-chloro-3-trifluoromethyl benzenesulfonylamino)-pyridine-2-carboxylic acid

Product 1

HCID 579424214-chloro-N-[5-chloro-2-(8-fluoro-2,3-dihydro-benzo[1,4]oxazine-4-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

8-Fluoro-3,4-dihydro-2H-benzo[1,4]oxazine, 5-chloro-3-(4-chloro-3-(trifluoromethyl)phenylsulfonamido)picolinic acid, T3P, and Et3N were reacted according to the procedure D to provide the title compound. HPLC purification provided 4-chloro-N-[5-chloro-2-(8-fluoro-2,3-dihydro-benzo[1,4]oxazine-4-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide. Reverse phase HPLC gradient acetonitrile 0.1% TFA 20-95% in 4 min: 2.986 min. MS m/z 550.1 (M+H).

Sources & evidence

ORD record
ord-8ae45ee0d3794448a716763499705ee9
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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