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

HRID 606071Notes

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 (7.6 g, 44 mmol) was added to a heated solution (40° C.) of 3-nitro-N-prop-2-ynyl[1,5]naphthyridin-4-amine (5.0 g, 22 mmol) and anhydrous triethylamine (6.7 mL, 48 mmol) in anhydrous dichloromethane (150 mL). The reaction was heated at 40° C. for 1.7 hours and then concentrated under reduced pressure. The residue was triturated with water; the resulting solid was isolated by filtration, washed sequentially with toluene and a small amount of diethyl ether, and then dissolved in dichloromethane. The solution was concentrated under reduced pressure and dried under high vacuum to provide 6.00 g of N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-3-nitro[1,5]naphthyridin-4-amine as a brownish-yellow solid.

Workup

concentrationconcentrated under reduced pressure
customThe residue was triturated with water
customthe resulting solid was isolated by filtration
washwashed sequentially with toluene
dissolutiona small amount of diethyl ether, and then dissolved in dichloromethane
concentrationThe solution was concentrated under reduced pressure
customdried under high vacuum

Sources & evidence

ORD record: ord-35cae8a4604a4c61a1785cff7f42b9b5
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915281B2

Reaction notes

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