Triethylamine → Tert-butyl 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)piperazine-1-carboxylate

HRID 1618750Notes

Reaction equation

Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[N:16]1([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(N(CC)CC)C>C(O)(C)C>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=[C:2]([N:19]2[CH2:18][CH2:17][N:16]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20]2)[C:11]=1[CH3:12]

Participants

Conditions

Temperature: 120 °C

Procedure

2,4-dichloro-5,7-difluoro-3-methylquinoline (4.90 g, 10.0 mmol), tert-butyl piperazine-1-carboxylate (3.70 g, 20.0 mmol) and triethylamine (2.80 mL, 20.0 mmol) were slurried in isopropyl alcohol (40 mL) and heated at 120° C. for 12 h. The reaction was then allowed to cool to rt and concentrated to dryness. The crude product was then purified by column chromatography (silica gel, 0 to 20% EtOAc:hexane) to give tert-butyl 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)piperazine-1-carboxylate. Mass Spectrum (ESI) m/e=398.2 (M+1).

Workup

temperatureto cool to rt
concentrationconcentrated to dryness
customThe crude product was then purified by column chromatography (silica gel, 0 to 20% EtOAc:hexane)

Sources & evidence

ORD record: ord-2ae4ec0cdd5144a3af39609ce933c19a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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