Methanesulfonyl chloride → (rac)-N-[4-(4-Trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-yl]-methanesulfonamide

HRID 714103Notes

Reaction equation

[F:1][C:2]([F:26])([F:25])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[CH2:16][CH2:15][CH:14]([NH:18][S:19]([CH:22]4CC4)(=[O:21])=[O:20])[C:13]=3[CH:12]=[N:11][CH:10]=2)=[CH:5][CH:4]=1.CS(Cl)(=O)=O>>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[CH2:16][CH2:15][CH:14]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[C:13]=3[CH:12]=[N:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 71811494(rac)-Cyclopropanesulfonic acid [4-(4-trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-yl]-amide

Product 1

HCID 71811493(rac)-N-[4-(4-Trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-yl]-methanesulfonamideYield 15%

Procedure

In analogy to the procedure described for the preparation of (rac)-cyclopropanesulfonic acid [4-(4-trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-yl]-amide (example 94), replacing cyclopropanesulfonyl chloride with methanesulfonyl chloride. The title compound was obtained as a light brown oil in 15% yield. MS: 357.4 (M+H)+.

Sources & evidence

ORD record: ord-312f0e3e673f4fafb3831cfdcd3b90bf
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187429B2

Reaction notes

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