Potassium → Cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-bromo-phenylamino)-2-methyl-benzooxazol-7-yl]-amide
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[C:13]([F:21])=[C:14]([F:20])[C:15]4[N:16]=[CH:17][O:18][C:19]=4[C:11]=3[N:10]([S:22]([CH:25]3[CH2:27][CH2:26]3)(=[O:24])=[O:23])C2=O)=[C:4]([F:29])[CH:3]=1.[K].F[C:32]1C2N=COC=2C(NS(C2CC2)(=O)=O)=C(NC2C=CC(I)=CC=2F)C=1F>>[F:20][C:14]1[C:15]2[N:16]=[C:17]([CH3:32])[O:18][C:19]=2[C:11]([NH:10][S:22]([CH:25]2[CH2:27][CH2:26]2)(=[O:23])=[O:24])=[C:12]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[F:29])[C:13]=1[F:21]Participants
4
Reactant 3
Product 1
Procedure
Compound 1G was prepared from 6-(4-bromo-2-fluoro-phenyl)-8-cyclopropanesulfonyl-4,5-difluoro-6,8-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazol-7-one (I-25a: 120 mg, 0.245 mmol) and potassium trimethylsilonolate (46 mg, 0.368 mmol) using procedures analogous to those described above for Compound 1A to afford 20 mg of the product (17.8% yield). H1NMR (DMSO-d6, 300 MHz): δ 9.75 (s, 1H), 8.90 (s, 1H), 7.80 (s, 1H), 7.52 (dd, 1H), 7.17 (d, 1H), 6.80-6.68 (m, 1H), 2.68-2.60 (m, 1H), 0.90-0.82 (m, 2H), 0.80-0.70 (m, 2H). LCMS: 96.25%, m/z=460.0 (M−2). HPLC: 96.94%
Sources & evidence
- ORD record
- ord-4fa98789eb33417a86574a1b35406dd9
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08614239B2
Reaction notes
Loading…