p-(Trifluoromethoxy)benzenesulphonyl chloride → N-[4-((1R,5S,6R)-3-Propionyl-3-aza-bicyclo[3.2.0]hept-6-yl)-phenyl]-4-trifluoromethoxy-benzenesulfonamide

HRID 1173063Notes

Reaction equation

HRID 1173063 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:14][C@@H:13]3[C@H:9]2[CH2:10][N:11]([C:15](=[O:18])[CH2:16][CH3:17])[CH2:12]3)=[CH:4][CH:3]=1.[F:19][C:20]([F:33])([F:32])[O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>>[C:15]([N:11]1[CH2:10][C@@H:9]2[C@@H:13]([CH2:14][C@H:8]2[C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:28]([C:25]3[CH:24]=[CH:23][C:22]([O:21][C:20]([F:19])([F:32])[F:33])=[CH:27][CH:26]=3)(=[O:30])=[O:29])=[CH:7][CH:6]=2)[CH2:12]1)(=[O:18])[CH2:16][CH3:17]

Participants

3

Reactant 2

HCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 673664421-[(1R,5S,6R)-6-(4-aminophenyl)-3-aza-bicyclo[3.2.0]hept-3-yl]-propan-1-one

Product 1

HCID 67366262N-[4-((1R,5S,6R)-3-Propionyl-3-aza-bicyclo[3.2.0]hept-6-yl)-phenyl]-4-trifluoromethoxy-benzenesulfonamideYield 86%

Procedure

Following a procedure analogous to the procedure described in example 1.5, but starting with 1-[(1R,5S,6R)-6-(4-aminophenyl)-3-aza-bicyclo[3.2.0]hept-3-yl]-propan-1-one and 4-trifluoromethoxybenzensulfonyl chloride, N-[4-((1R,5S,6R)-3-propionyl-3-azabicyclo[3.2.0]hept-6-yl)-phenyl]-4-trifluoromethoxy-benzenesulfonamide (234 mg, yield 86%) was obtained.

Sources & evidence

ORD record
ord-72801e6371154f4a8549dfc54361bac0
Source dataset
uspto-grants-2010_11
Patent number
US07834048B2

Reaction notes

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