Triethylamine → HCID 59002849, compound

HRID 561113Notes

Reaction equation

[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[C:10]([F:17])=[C:11](F)[C:12]=3[O:14][CH3:15])[C:7](=[O:25])[C:6]([C:26]#[N:27])=[CH:5]2)[CH2:3][CH2:2]1.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][CH2:35][CH2:36][NH2:37].C(N(CC)CC)C>CS(C)=O>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[C:10]([F:17])=[C:11]([NH:37][CH2:36][CH2:35][NH:34][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=4)[C:12]=3[O:14][CH3:15])[C:7](=[O:25])[C:6]([C:26]#[N:27])=[CH:5]2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-5-(trifluoroacetamido) quinoline-3-carbonitrile (500 mg, 1.29 mmol), N-2-pyridyl-1,2-ethanediamine (354 mg, 2.58 mmol) and triethylamine (0.36 mL, 2.58 mmol) in anhydrous DMSO (8 mL) was stirred at 60° C. for 16 h. After cooling, the reaction mixture was poured into ice-water (50 mL). The resulting precipitate was collected by filtration, washed with water and then dried. The crude product was purified by column chromatography (Hexane:EtOAc 1:1→2:3→EtOAc→CH2Cl2: MeOH 8:1) to give 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-[2-(2-pyridylamino)ethylamino]-5-(trifluoroacetamido)quinoline-3-carbonitrile (276 mg, 42%) as a brown solid.

Workup

temperatureAfter cooling
filtrationThe resulting precipitate was collected by filtration
washwashed with water
customdried
customThe crude product was purified by column chromatography (Hexane:EtOAc 1:1→2:3→EtOAc→CH2Cl2: MeOH 8:1)

Sources & evidence

ORD record: ord-27b6371cc0cb42b8847f470e96d086d4
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063221B2

Reaction notes

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