1-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chloride → 8-(1-Allyl-cyclopropanesulfonyl)-4,5-difluoro-6-(2-fluoro-4-iodo-phenyl)-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-one

HRID 1914883Notes

Reaction equation

HRID 1914883 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].[CH2:24]([C:27]1([S:30](Cl)(=[O:32])=[O:31])[CH2:29][CH2:28]1)[CH:25]=[CH2:26]>CN(C1C=CN=CC=1)C>[CH2:24]([C:27]1([S:30]([N:11]2[C:5]3[C:6]4[O:10][CH:9]=[N:8][C:7]=4[C:2]([F:1])=[C:3]([F:23])[C:4]=3[N:13]([C:14]3[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=3[F:21])[C:12]2=[O:22])(=[O:32])=[O:31])[CH2:29][CH2:28]1)[CH:25]=[CH2:26]

Participants

4

Reactant 2

HCID 441819591-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chlorideHCID 67253227HCID 67253227, compound

Product 1

HCID 683133558-(1-Allyl-cyclopropanesulfonyl)-4,5-difluoro-6-(2-fluoro-4-iodo-phenyl)-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-oneYield 55.8%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Intermediate I-21a 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: 250 mg, 0.561 mmol), 1-allyl-cyclopropanesulfonyl chloride (202 mg, 1.12 mmol), TEA (228 mL, 1.68 mmol) and DMAP (25 mg) using procedures analogous to those described above for Intermediate I-19a to afford 180 mg of the product (55.3% yield).

Sources & evidence

ORD record
ord-dc7d5fb61a9b48f09312e91fb9cad911
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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