Potassium → 1-Allyl-cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-iodo-phenylamino)-benzooxazol-7-yl]-amide
Reaction equation
[CH2:1]([C:4]1([S:7]([N:10]2[C:14]3[C:15]4[O:19][CH:18]=[N:17][C:16]=4[C:20]([F:23])=[C:21]([F:22])[C:13]=3[N:12]([C:24]3[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=3[F:31])C2=O)(=[O:9])=[O:8])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[K].FC1C2N=COC=2C(NS(C2CC2)(=O)=O)=C(NC2C=CC(I)=CC=2F)C=1F>>[F:23][C:20]1[C:16]2[N:17]=[CH:18][O:19][C:15]=2[C:14]([NH:10][S:7]([C:4]2([CH2:1][CH:2]=[CH2:3])[CH2:6][CH2:5]2)(=[O:9])=[O:8])=[C:13]([NH:12][C:24]2[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=2[F:31])[C:21]=1[F:22]Participants
4
Reactant 3
Product 1
Procedure
Compound 1D was prepared from 8-(1-allyl-cyclopropanesulfonyl)-4,5-difluoro-6-(2-fluoro-4-iodo-phenyl)-6,8-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazol-7-one (I-21a: 210 mg, 0.365 mmol) and potassium trimethylsilonolate (50 mg, 0.390 mmol) using procedures analogous to those described above for Compound 1A to afford 150 mg of the product (75% yield). H1NMR (CDCl3, 300 MHz): δ 8.13 (s, 1H), 7.42 (dd, 1H), 7.31-7.25 (m, 1H), 6.80 (s, 1H), 6.43-6.35 (m, 1H), 6.21 (s, 1H), 5.85-5.70 (m, 1H), 5.22-5.14 (m, 2H), 2.83 (d, 2H), 1.28-1.20 (m, 2H), 0.87-0.80 (m, 2H). LCMS: 97.9%, m/z=548.0 (M−1). HPLC: 86.29%.
Sources & evidence
- ORD record
- ord-61d47d2ee47a4baa9e12c33e2806bb94
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08614239B2
Reaction notes
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