Triethylamine → 2-chloro-N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-3-nitroquinolin-4-amine

HRID 606102Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](Cl)=[N:9][OH:10])=[CH:4][CH:3]=1.[Cl:12][C:13]1[C:22]([N+:23]([O-:25])=[O:24])=[C:21]([NH:26][CH2:27][C:28]#[CH:29])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.C(N(CC)CC)C>ClCCl>[Cl:12][C:13]1[C:22]([N+:23]([O-:25])=[O:24])=[C:21]([NH:26][CH2:27][C:28]2[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:29]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Under a nitrogen atmosphere, 4-fluoro-N-hydroxybenzenecarboximidoyl chloride (54 g, 230 mmol), prepared as described in Parts A through C of Example 11, was added to a solution of 2-chloro-3-nitro-N-prop-2-ynylquinolin-4-amine (30.2 g, 115 mmol), prepared as described in Part A of Example 3, in dichloromethane (1 L) at room temperature. Triethylamine (26 g, 250 mmol) was added; a precipitate formed. The resulting mixture was heated at 40° C. under nitrogen for 16.5 hours and concentrated under reduced pressure. The resulting solid was dissolved in ethyl acetate, and the work-up and isolation procedures described in Part B of Example 18 were followed to provide 36.12 g of 2-chloro-N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-3-nitroquinolin-4-amine as a yellow solid.

Workup

customprepared
customat room temperature
customa precipitate formed
concentrationconcentrated under reduced pressure
dissolutionThe resulting solid was dissolved in ethyl acetate

Sources & evidence

ORD record: ord-2cf3afc2f61140ec91aefbea86625639
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915281B2

Reaction notes

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