Sodium hydride → 6-(4-Bromo-2-fluoro-phenyl)-4,5-difluoro-7-oxo-6,7-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazole-8-sulfonic acid dimethylamide

HRID 1914886Notes

Reaction equation

HRID 1914886 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[NH:10][C:9]2=[O:22])=[C:4]([F:23])[CH:3]=1.[CH3:24][N:25]([CH3:30])[S:26](Cl)(=[O:28])=[O:27].[H-].[Na+]>>[CH3:24][N:25]([CH3:30])[S:26]([N:10]1[C:11]2[C:19]3[O:18][CH:17]=[N:16][C:15]=3[C:14]([F:20])=[C:13]([F:21])[C:12]=2[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[F:23])[C:9]1=[O:22])(=[O:28])=[O:27]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 672366336-(4-Bromo-2-fluoro-phenyl)-4,5-difluoro-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-one

Product 1

HCID 683135286-(4-Bromo-2-fluoro-phenyl)-4,5-difluoro-7-oxo-6,7-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazole-8-sulfonic acid dimethylamideYield 14.5%

Procedure

Intermediate I-24a was prepared from 6-(4-bromo-2-fluoro-phenyl)-4,5-difluoro-6,8-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazol-7-one (I-16a: 350 mg, 0911 mmol), N,N-dimethylaminosulfonyl chloride (196.32 mg, 1.36 mmol) and NaH (54.4 mg, 1.36 mmol) using procedures analogous to those described above for Intermediate I-19a to afford 65 mg of the product (14.5% yield). H1NMR (DMSO-d6, 300 MHz): δ 8.96 (s, 1H), 7.95 (dd, 1H), 7.79 (t, 1H), 7.69 (dd, 1H), 3.08 (s, 6H). HPLC: 95.7%

Sources & evidence

ORD record
ord-441fa4ecfdb94352b711d081cc32599f
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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