Pyridine → 2-Oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonic acid phenylamide

HRID 1743286Notes

Reaction equation

HRID 1743286 reaction equation
[O:1]=[C:2]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:16](Cl)(=[O:18])=[O:17])[CH:8]=2)[NH:3]1.[C:20]1([NH2:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=CC=CC=1>>[C:20]1([NH:26][S:16]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[NH:3][C:2](=[O:1])[CH:11]=[C:10]3[C:12]([F:15])([F:14])[F:13])(=[O:18])=[O:17])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 6115AnilineHCID 220553102-Oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonyl chloride

Product 1

HCID 104741742-Oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonic acid phenylamideYield 18.7%

Procedure

Following the same procedure as Example 1, condensation of 2-oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonyl chloride (Preparation 3, 50 mg, 160 μmol) with PhNH2 (15 μL, 168 μmol), employing pyridine (14 μL, 168 μmol) as base, gave the title compound (11 mg, 17%): δH ((CD3)2SO)=7.00 (s, 1H), 7.05–7.10 (m, 3H), 7.20 (m, 2H), 7.50 (d, 1H), 7.90 (dd, 1H), 8.00 (d, 1H); m/z (ES+)=369.1 [M+H]+.

Sources & evidence

ORD record
ord-0aeb149c060b41cca1cb86f9623a2634
Source dataset
uspto-grants-2006_03
Patent number
US07009052B2

Reaction notes

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