Piperidine → 6-(Piperidine-1-sulfonyl)-4-trifluoromethyl-1H-quinolin-2-one

HRID 1829901Notes

Reaction equation

HRID 1829901 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.[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.CCN(CC)CC>>[N:20]1([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])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 220553102-Oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonyl chloride

Product 1

HCID 99757716-(Piperidine-1-sulfonyl)-4-trifluoromethyl-1H-quinolin-2-oneYield 43.4%

Procedure

Condensation of 2-oxo-4-trifluoromethyl-1,2-dihydroquinoline-6-sulfonyl chloride (Preparation 3, 50 mg, 160 μmol) with piperidine (17 μL, 168 μmol), employing NEt3 (23 μL, 168 μmol) as base as outlined for Example 1, gave the title compound (25 mg, 42%): δH ((CD3)2SO)=1.30–1.40 (m, 2H), 1.50–1.60 (m, 4H), 2.90 (t, 4H), 7.15 (s, 1H), 7.60 (d, 1H), 7.90–8.00 (m, 2H); m/z (ES+)=361.0 [M+H]+.

Sources & evidence

ORD record
ord-16a38e69766745078a40ebe3cd14c86d
Source dataset
uspto-grants-2006_06
Patent number
US07064207B2

Reaction notes

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