2,5-Dichlorothiophene-3-sulfonyl chloride → (r)-2,5-Dichloro-thiophene-3-sulfonic acid [1-(5'-fluoro-2'-methoxy-biphenyl-4-yl)-ethyl]-amide

HRID 2422851Notes

Reaction equation

HRID 2422851 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(C3C=C(C)OC=3C)(=O)=O)[CH3:15])=[CH:10][CH:9]=2)[CH:7]=1.[Cl:29][C:30]1[S:31][C:32]([Cl:39])=[CH:33][C:34]=1[S:35](Cl)(=[O:37])=[O:36].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:35]([C:34]3[CH:33]=[C:32]([Cl:39])[S:31][C:30]=3[Cl:29])(=[O:37])=[O:36])[CH3:15])=[CH:10][CH:9]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 27360942,5-Dichlorothiophene-3-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 24768972(r)-2,5-Dichloro-thiophene-3-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 2,5-dichloro-3-thiophenesulfonyl chloride and 1-(5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethylamine. Title compound: 1H NMR (400 MHz, CDCl3): δ 7.40, 7.18 (a/b, 4H), 7.05-6.88 (m, 4H), 5.05 (d, 1H), 4.60 (m, 1H), 3.78 (s, 3H), 1.54 (d, 3H) ppm; MS (ESI) m/z: 482 [M+Na]+.

Sources & evidence

ORD record
ord-052eedb2a76c4be4b7676cafd546bfee
Source dataset
uspto-grants-2011_06
Patent number
US07960365B2

Reaction notes

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