Lithium Hydroxide → Cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-bromo-phenylamino)-2-methyl-benzooxazol-7-yl]-amide

HRID 1914904Notes

Reaction equation

HRID 1914904 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[C:13]([F:22])=[C:14]([F:21])[C:15]4[N:16]=[C:17]([CH3:20])[O:18][C:19]=4[C:11]=3[N:10]([S:23]([CH:26]3[CH2:28][CH2:27]3)(=[O:25])=[O:24])C2=O)=[C:4]([F:30])[CH:3]=1.[Li+].[OH-].FC1C2N=COC=2C(NS(C2CC2)(=O)=O)=C(NC2C=CC(I)=CC=2F)C=1F>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:12]2[C:13]([F:22])=[C:14]([F:21])[C:15]3[N:16]=[C:17]([CH3:20])[O:18][C:19]=3[C:11]=2[NH:10][S:23]([CH:26]2[CH2:28][CH2:27]2)(=[O:24])=[O:25])=[C:4]([F:30])[CH:3]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 53241452Cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-iodo-phenylamino)-benzooxazol-7-yl]-amideHCID 672372936-(4-Bromo-2-fluoro-phenyl)-8-cyclopropanesulfonyl-4,5-difluoro-2-methyl-6,8-dihydro-imidazo [4',5':3,4]benzo[1,2-d]oxazol-7-one

Product 1

HCID 53241562Cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-bromo-phenylamino)-2-methyl-benzooxazol-7-yl]-amide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 1H was prepared from 6-(4-bromo-2-fluoro-phenyl)-8-cyclopropanesulfonyl-4,5-difluoro-2-methyl-6,8-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazol-7-one (I-26a: 100 mg, 0.2 mmol) and LiOH (50 mg, 1.25 mmol) in water (2 mL) using procedures analogous to those described above for Compound 1A to afford 30 mg of the product (31.57% yield). H1NMR (CDCl3, 300 MHz): δ 7.30-7.24 (m, 1H), 7.11 (dt, 1H), 6.56 (s, 1H), 6.54-6.46 (m, 1H), 6.33 (s, 1H), 2.70 (s, 3H), 2.68-2.60 (m, 1H), 1.24-1.16 (m, 2H), 1.04-0.96 (m, 2H). LCMS: 95.35%, m/z=474.0 (M-2). HPLC: 93.89%

Sources & evidence

ORD record
ord-f551a3a104384ff9929b476c81725730
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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