Benzylamine → 2-Oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonic acid benzylamide

HRID 1743287Notes

Reaction equation

HRID 1743287 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.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN(CC)CC>>[CH2:20]([NH:27][S:16]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])[CH:11]=[C:10]2[C:12]([F:15])([F:14])[F:13])(=[O:18])=[O:17])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 220553102-Oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonyl chloride

Product 1

HCID 100912812-Oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonic acid benzylamideYield 92.3%

Procedure

Condensation of 2-oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonyl chloride (Preparation 3, 16 mg, 51 μmol) with BnNH2 (7 μL, 54 μmol), employing NEt3 (8 μL, 57 μmol) as base as delineated in Example 1, gave the title compound (18 mg, 90%): δH ((CD3)2SO) =4.00 (d, 2H), 7.05 (s, 1H), 7.10–7.20 (m, 5H), 7.50 (d, 1H), 7.95 (dd, 1H), 8.00 (d, 1H), 8.30 (t, 1H); m/z (ES−)=381.0 [M−H]−.

Sources & evidence

ORD record
ord-ef44e740eaa74e408f73c3070e0c1385
Source dataset
uspto-grants-2006_03
Patent number
US07009052B2

Reaction notes

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