Potassium → Cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-iodo-phenylamino)-2-methyl-benzooxazol-7-yl]amide
Reaction equation
[CH:1]1([S:4]([N:7]2[C:11]3[C:12]4[O:16][C:15]([CH3:17])=[N:14][C:13]=4[C:18]([F:21])=[C:19]([F:20])[C:10]=3[N:9]([C:22]3[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=3[F:29])C2=O)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[K].FC1C2N=COC=2C(NS(C2CC2)(=O)=O)=C(NC2C=CC(I)=CC=2F)C=1F>>[F:21][C:18]1[C:13]2[N:14]=[C:15]([CH3:17])[O:16][C:12]=2[C:11]([NH:7][S:4]([CH:1]2[CH2:3][CH2:2]2)(=[O:6])=[O:5])=[C:10]([NH:9][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])[C:19]=1[F:20]Participants
4
Reactant 3
Product 1
Procedure
Compound 1E was prepared from 8-cyclopropanesulfonyl-4,5-difluoro-6-(2-fluoro-4-iodo-phenyl)-2-methyl-6,8-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazol-7-one (I-22a: 55 mg, 0.12 mmol) and potassium trimethylsilonolate (30 mg, 0.18 mmol) using procedures analogous to those described above for Compound 1A to afford 3 mg of the product (5.66% yield). H1NMR (CDCl3, 300 MHz): δ 7.40 (d, 1H), 7.30-7.22 (m, 1H), 6.59 (s, 1H), 6.49 (s, 1H), 6.40-6.30 (m, 1H), 2.70 (s, 3H), 2.66-2.58 (m, 1H), 1.22-1.14 (m, 2H), 1.04-0.94 (m, 2H). LCMS: 82.6%, m/z=523.6 (M+1). HPLC: 99.35%.
Sources & evidence
- ORD record
- ord-d5d41375c8db43bebf06c9da61a74fe2
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08614239B2
Reaction notes
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