Potassium → Dimethylsulfamic acid [4,5-difluoro-6-(2-fluoro-4-bromo-phenylamino)-benzooxazol-7-yl]-amide
Reaction equation
[CH3:1][N:2]([CH3:29])[S:3]([N:6]1[C:10]2[C:11]3[O:15][CH:14]=[N:13][C:12]=3[C:16]([F:19])=[C:17]([F:18])[C:9]=2[N:8]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=2[F:27])C1=O)(=[O:5])=[O:4].[K].FC1C2N=COC=2C(NS(C2CC2)(=O)=O)=C(NC2C=CC(I)=CC=2F)C=1F>>[F:19][C:16]1[C:12]2[N:13]=[CH:14][O:15][C:11]=2[C:10]([NH:6][S:3](=[O:5])(=[O:4])[N:2]([CH3:29])[CH3:1])=[C:9]([NH:8][C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=2[F:27])[C:17]=1[F:18]Participants
4
Reactant 3
Product 1
Procedure
Compound 1F was prepared from 6-(4-bromo-2-fluoro-phenyl)-4,5-difluoro-7-oxo-6,7-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazole-8-sulfonic acid dimethylamide (I-24a: 100 mg, 0.203 mmol) and potassium trimethylsilonolate (39 mg, 0.305 mmol) using procedures analogous to those described above for Compound 1A to afford 30 mg of the product (29% yield). H1NMR (CDCl3, 300 MHz): δ 8.14 (s, 1H), 7.11-7.24 (m, 2H), 7.12 (dt, 1H), 6.79 (s, 1H), 6.58-6.48 (m, 1H), 2.90 (s, 6H). LCMS: 95.77%, m/z=462.9 (M−2). HPLC: 96.26%
Sources & evidence
- ORD record
- ord-99d712d2b7524772bbcea9e2daae0204
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08614239B2
Reaction notes
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