1-(difluoromethyl)-3,5-dimethyl-1H-pyrazole-4-sulfonyl chloride → (r)-1-Difluoromethyl-3,5-dimethyl-1h-pyrazole-4-sulfonic acid [1-(2'-trifluoromethoxy-biphenyl-4-yl)-ethyl]-amide

HRID 2422875

Reaktionsgleichung

Reaktionsgleichung von HRID 2422875
FC1C=CC(OC)=C(C2C=CC([C@H](NS(C3C=C(C)OC=3C)(=O)=O)C)=CC=2)C=1.[F:29][CH:30]([F:42])[N:31]1[C:35]([CH3:36])=[C:34]([S:37](Cl)(=[O:39])=[O:38])[C:33]([CH3:41])=[N:32]1.[F:43][C:44]([F:62])([F:61])[O:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[C:52]1[CH:57]=[CH:56][C:55]([CH:58]([NH2:60])[CH3:59])=[CH:54][CH:53]=1>>[F:43][C:44]([F:61])([F:62])[O:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[C:52]1[CH:57]=[CH:56][C:55]([C@H:58]([NH:60][S:37]([C:34]2[C:33]([CH3:41])=[N:32][N:31]([CH:30]([F:42])[F:29])[C:35]=2[CH3:36])(=[O:39])=[O:38])[CH3:59])=[CH:54][CH:53]=1

Komponenten

4

Edukt 3

HCID 64854211-(difluoromethyl)-3,5-dimethyl-1H-pyrazole-4-sulfonyl chlorideHCID 24768970(r)-2,5-Dimethyl-furan-3-sulfonic acid [1-(5'-fluoro-2'-methoxy-biphenyl-4-yl)-ethyl]-amideHCID 610328391-(2'-Trifluoromethoxy-biphenyl-4-yl)-ethylamine

Produkt 1

HCID 67244507(r)-1-Difluoromethyl-3,5-dimethyl-1h-pyrazole-4-sulfonic acid [1-(2'-trifluoromethoxy-biphenyl-4-yl)-ethyl]-amide

Versuchsvorschrift

Prepared in a similar manner to (R)-2,5-dimethyl-furan-3-sulfonic acid [1-(5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethyl]-amide (Example 10) starting with 1-difluoromethyl-3,5-dimethylpyrazole-4-sulfonyl chloride and 1-(2′-trifluoromethoxy-biphenyl-4-yl)-ethylamine. Title compound: 1H NMR (400 MHz, CDCl3): δ 7.43-7.11 (m, 8H), 6.99 (s, 1H), 4.86 (s, 1H), 4.58 (m, 1H), 2.45 (s, 3H), 2.30 (s, 3H), 1.54 (d, 3H), ppm; MS (ESI) m/z: 490 [M+H]+.

Quellen und Nachweise

ORD-Eintrag
ord-9c84bcdbc2f340e8995f3c8386cab368
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960365B2

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