Potassium → Dimethylsulfamic acid [4,5-difluoro-6-(2-fluoro-4-iodo-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]([I: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]([I:26])=[CH:22][C:21]=2[F:27])[C:17]=1[F:18]Participants
4
Reactant 3
Product 1
Procedure
Compound 1C was prepared from 4,5-difluoro-6-(2-fluoro-4-iodo-phenyl)-7-oxo-6,7-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazole-8-sulfonic acid dimethylamide (60 mg, 0.12 mmol) and potassium trimethylsilonolate (30 mg, 0.18 mmol) using procedures analogous to those described above for Compound 1A to afford 30 mg of the product (49% yield). H1NMR (CDCl3, 300 MHz): δ 8.15 (s, 1H), 7.44 (dd, 1H), 7.29 (d, 1H), 6.82 (s, 1H), 6.45-6.35 (m, 1H), 6.19 (s, 1H), 2.88 (s, 6H). LCMS: 81.2%, m/z=510.9 (M−1). HPLC: 80.5%.
Sources & evidence
- ORD record
- ord-1e348fa96f294086a21ccfa9c4d3afae
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08614239B2
Reaction notes
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