Pyridine → HCID 56966500, compound

HRID 1036983Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1)[CH2:6][C:5]2([CH3:23])[CH3:22].N1C=CC=CC=1.[F:30][C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([S:18]([NH:37][C:34]3[CH:35]=[CH:36][C:31]([F:30])=[CH:32][CH:33]=3)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1)[CH2:6][C:5]2([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

3-(6-Chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-benzenesulfonyl chloride (204 mg 0.55 mmol) was dissolved in dichloromethane (5 mL). Pyridine (5 mL) was added to the mixture and cooled to 0° C. 4-fluoro-phenylamine (61 mg, 0.55 mmol) was added. The mixture was stirred at room temperature for 2 h. Solvent was removed and the residue was purified on thin layer chromatography using petroleum ether/ethyl acetate=3:1 as eluent to afford 3-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-N-(4-fluoro-phenyl)-benzenesulfonamide as white solid (89 mg, 37% yield). MS (ESI+APCI) M+1=445.1.

Workup

customSolvent was removed
customthe residue was purified on thin layer chromatography

Sources & evidence

ORD record: ord-4b028e66b45f4603b1cfeef78a9613d1
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546427B2

Reaction notes

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