4-Fluorobenzylamine → HCID 59486216, compound

HRID 1949178Notes

Reaction equation

C[Al](C)C.[F:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1.C([O:16][C:17]([C:19]1[C:20]([S:35][CH2:36][CH3:37])=[N:21][C:22]2[C:27]([C:28]=1[CH3:29])=[CH:26][CH:25]=[C:24]([O:30][C:31]([F:34])([F:33])[F:32])[CH:23]=2)=O)C.CCCCCC.C(Cl)Cl>C1(C)C=CC=CC=1.Cl>[CH2:36]([S:35][C:20]1[C:19]([C:17]([NH:11][CH2:10][C:9]2[CH:12]=[CH:13][C:6]([F:5])=[CH:7][CH:8]=2)=[O:16])=[C:28]([CH3:29])[C:27]2[C:22](=[CH:23][C:24]([O:30][C:31]([F:34])([F:32])[F:33])=[CH:25][CH:26]=2)[N:21]=1)[CH3:37]

Participants

Conditions

Temperature: 90 °C

Procedure

1.12 ml (2.24 mmol, 2M in toluene)trimethyl aluminium and 260 μl (2.24 mmol) 4-fluorobenzylamine were added in succession to a solution of 200 mg (0.56 mmol) 2-ethylsulfanyl-4-methyl-7-(trifluoromethyloxy)-quinoline-3-carboxylic acid ethyl ester (VVV25) in toluene (7 ml) and the mixture was then heated for 3 h at 90° C. Then it was diluted with 0.5M hydrochloric acid and extracted with EE. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/DCM 3:2) of the residue yielded 150 mg (0.34 mmol, 61%) 2-ethylsulfanyl-N-[(4-fluorophenyl)-methyl]-4-methyl-7-(trifluoromethyloxy)-quinoline-3-carboxamide. MS: m/z 439.1 [M+H]+.

Workup

extractionextracted with EE
washThe organic phase was washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record: ord-680c8c25a2c6424ab4b138f767d6aa06
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399673B2

Reaction notes

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