Cyclopropanesulfonyl chloride → HCID 67246005, compound

HRID 1914884Notes

Reaction equation

HRID 1914884 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].[CH:25]1([S:28](Cl)(=[O:30])=[O:29])[CH2:27][CH2:26]1>CN(C1C=CN=CC=1)C>[CH:25]1([S:28]([N:12]2[C:5]3[C:6]4[O:10][C:9]([CH3:11])=[N:8][C:7]=4[C:2]([F:1])=[C:3]([F:24])[C:4]=3[N:14]([C:15]3[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=3[F:22])[C:13]2=[O:23])(=[O:30])=[O:29])[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 2760919Cyclopropanesulfonyl 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 67246005HCID 67246005, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Intermediate I-22a 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), cyclopropanesulfonyl chloride (37.75 mg, 0.269 mmol), TEA (54.46 mg, 0.534 mmol) and DMAP (10 mg) using procedures analogous to those described above for Intermediate I-19a to afford 55 mg of the product (56.3% yield). H1NMR (CDCl3, 300 MHz): δ 7.72-7.64 (m, 2H), 7.30-7.22 (m, 1H), 3.34-3.24 (m, 1H), 2.74 (s, 3H), 1.74-1.60 (m, 2H), 1.34-1.20 (m, 2H). LCMS: 81.9%; 549.9 (M+1).

Sources & evidence

ORD record
ord-5e492d7c9de343518028e82c4f47ca20
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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