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

HRID 2422852Notes

Reaction equation

HRID 2422852 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C@H:14]([NH:16][S:17]([C:20]3[CH:24]=[C:23](C)O[C:21]=3C)(=[O:19])=[O:18])[CH3:15])=[CH:10][CH:9]=2)[CH:7]=1.[CH3:29][N:30]1C=C(S(Cl)(=O)=O)C(C)=[N:31]1.FC1C=CC(OC)=C(C2C=CC(C(N)C)=CC=2)C=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C@H:14]([NH:16][S:17]([C:20]3[C:24]([CH3:23])=[N:31][N:30]([CH3:29])[CH:21]=3)(=[O:19])=[O:18])[CH3:15])=[CH:10][CH:9]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 46357071,3-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 610332941-(5'-Fluoro-2'-methoxy-biphenyl-4-yl)-ethylamine

Product 1

HCID 24768973(r)-1,3-Dimethyl-1h-pyrazole-4-sulfonic acid [1-(5'-fluoro-2'-methoxy-biphenyl-4-yl)-ethyl]-amide

Procedure

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 1,3-dimethyl-1H-pyrazole-4-sulfonyl chloride and 1-(5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethylamine. Title compound: 1H NMR (400 MHz, CDCl3): δ 7.41, 7.20 (a/b, 4H), 7.39 (s, 1H), 7.05-6.88 (m, 3H), 4.70 (d, 1H), 4.55 (m, 1H), 3.78 (s, 3H), 3.69 (s, 3H), 2.33 (s, 3H), 1.52 (d, 3H) ppm; MS (ESI) m/z: 404 [M+H]+.

Sources & evidence

ORD record
ord-0d0a499be57049a1912683cb87a8f405
Source dataset
uspto-grants-2011_06
Patent number
US07960365B2

Reaction notes

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