Dimethylsulphamoyl chloride → 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

HRID 1914882Notes

Reaction equation

HRID 1914882 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[CH:9][O:10][C:6]=2[C:5]2[NH:11][C:12](=[O:22])[N:13]([C:14]3[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=3[F:21])[C:4]=2[C:3]=1[F:23].[CH3:24][N:25]([CH3:30])[S:26](Cl)(=[O:28])=[O:27]>CN(C1C=CN=CC=1)C>[CH3:24][N:25]([CH3:30])[S:26]([N:11]1[C:5]2[C:6]3[O:10][CH:9]=[N:8][C:7]=3[C:2]([F:1])=[C:3]([F:23])[C:4]=2[N:13]([C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[F:21])[C:12]1=[O:22])(=[O:28])=[O:27]

Participants

4

Reactant 2

HCID 83372Dimethylsulphamoyl chlorideHCID 67253227HCID 67253227, compound

Product 1

HCID 672377864,5-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 dimethylamideYield 60.3%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Intermediate I-20a was prepared from 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-15a: 80 mg, 0.185 mmol), N,N-dimethylaminosulfonyl chloride (41 mg, 0.277 mmol), TEA (78 mg, 0.55 mmol) and DMAP (10 mg) using procedures analogous to those described above for Intermediate I-19a to afford 60 mg of the product (60% yield). H1NMR (CDCl3, 300 MHz): δ 8.16 (s, 1H), 7.72-7.69 (m, 1H), 7.68-7.65 (m, 1H), 7.29-7.22 (m, 1H), 3.2 (s, 6H).

Sources & evidence

ORD record
ord-01c65fa867b14738bf73d4c54b278210
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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