Ethylamine hydrochloride → HCID 56846699, compound

HRID 1260701Notes

Reaction equation

Cl[C:2]1[C:11]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[O:13])=[C:10]([CH3:23])[C:9]2[C:4](=[CH:5][C:6]([C:24]([F:27])([F:26])[F:25])=[CH:7][CH:8]=2)[N:3]=1.Cl.[CH2:29]([NH2:31])[CH3:30].CCN(C(C)C)C(C)C.[OH-].[Na+]>CCOC(C)=O.CC#N>[CH2:29]([NH:31][C:2]1[C:11]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[O:13])=[C:10]([CH3:23])[C:9]2[C:4](=[CH:5][C:6]([C:24]([F:27])([F:26])[F:25])=[CH:7][CH:8]=2)[N:3]=1)[CH3:30]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 238 mg (0.6 mmol) 2-chloro-N-(3-fluorobenzyl)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid amide, 146 mg (1.8 mmol) ethylamine hydrochloride, 469 μl (2.7 mmol) DIPEA and MeCN (1,6 ml) was heated in a sealed vessel with microwave radiation to 180° C. for 2 h. After cooling to RT, dilution was carried out with EtOAc (30 ml) and a 2M aq. NaOH sol. (5 ml). The organic phase was then separated, washed with water and brine, dried over MgSO4 and concentrated in a vacuum. After column chromatographic separation (silica gel, EtOAc/hexane 3:7) of the residue, 188 mg (0.5 mmol, 77%) 2-ethylamino-N-[(3-fluorophenyl)-methyl]-4-methyl-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide (example 1) was obtained. MS: m/z 406.1 [M+H]+.

Workup

temperatureAfter cooling to RT
customThe organic phase was then separated
washwashed with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in a vacuum
customAfter column chromatographic separation (silica gel, EtOAc/hexane 3:7) of the residue

Sources & evidence

ORD record: ord-9ea9c2793e614d2f908b293470152418
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470852B2

Reaction notes

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