Triethylamine → N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-3-nitro[1,5]naphthyridin-4-amine

HRID 606074Notes

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

Participants

Conditions

Temperature: 40 °C

Procedure

Under a nitrogen atmosphere, 4-fluoro-N-hydroxybenzenecarboximidoyl chloride (44.6 g, 257 mmol) was added to a mixture of 3-nitro-N-prop-2-ynyl[1,5]naphthyridin-4-amine (29.34 g, 129 mmol) and anhydrous triethylamine (39.5 mL, 283 mmol) in anhydrous dichloromethane (1 L). The reaction was stirred at 40° C. for 18 hours and then concentrated under reduced pressure. The residue was triturated with water; the resulting solid was isolated by filtration, washed sequentially with isopropanol and a small amount of diethyl ether, and then dried under vacuum to provide 15.02 g of N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-3-nitro[1,5]naphthyridin-4-amine as a brownish-green solid.

Workup

concentrationconcentrated under reduced pressure
customThe residue was triturated with water
customthe resulting solid was isolated by filtration
washwashed sequentially with isopropanol
dry with materiala small amount of diethyl ether, and then dried under vacuum

Sources & evidence

ORD record: ord-949fc96ab45747949bd4864a7d0908bf
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915281B2

Reaction notes

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