Dimethylsulphamoyl chloride → HCID 67235634, compound

HRID 1914885Notes

Reaction equation

HRID 1914885 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[O:10][C:6]=2[C:5]2[NH:12][C:13](=[O:23])[N:14]([C:15]3[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=3[F:22])[C:4]=2[C:3]=1[F:24].[CH3:25][N:26]([CH3:31])[S:27](Cl)(=[O:29])=[O:28]>CN(C1C=CN=CC=1)C>[CH3:25][N:26]([CH3:31])[S:27]([N:12]1[C:5]2[C:6]3[O:10][C:9]([CH3:11])=[N:8][C:7]=3[C:2]([F:1])=[C:3]([F:24])[C:4]=2[N:14]([C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=2[F:22])[C:13]1=[O:23])(=[O:29])=[O:28]

Participants

4

Reactant 2

HCID 83372Dimethylsulphamoyl chlorideHCID 672384834,5-Difluoro-6-(2-fluoro-4-iodo-phenyl)-2-methyl-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-one

Product 1

HCID 67235634HCID 67235634, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Intermediate I-23a was prepared from 4,5-difluoro-6-(2-fluoro-4-iodo-phenyl)-2-methyl-6,8-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazol-7-one (I-18a: 80 mg, 0.178 mmol), N,N-dimethylaminosulfonyl chloride (38.5 mg, 0.269 mmol), TEA (54.5 mg, 0.534 mmol) and DMAP (10 mg) using procedures analogous to those described above for Intermediate I-19a to afford the 60 mg of the product (61.2% yield). H1NMR (CDCl3, 300 MHz): δ 7.70-7.64 (m, 2H), 7.30-7.22 (m, 1H), 3.20 (s, 6H), 2.72 (s, 3H). LCMS: 70.3%, m/z=552.9 (M+1). HPLC: 81.3%.

Sources & evidence

ORD record
ord-edd7c9f425ec46bcbfc225080f088175
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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