Triethylamine → HCID 57455387, compound

HRID 1623092Notes

Reaction equation

C(N(CC)CC)C.Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[N:12]=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20].[CH2:22]([O:24][CH:25]([O:30][CH2:31][CH3:32])[CH2:26][CH2:27][CH2:28][NH2:29])[CH3:23]>ClCCl.C(=O)(O)[O-].[Na+]>[CH2:31]([O:30][CH:25]([O:24][CH2:22][CH3:23])[CH2:26][CH2:27][CH2:28][NH:29][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[N:12]=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20])[CH3:32]

Participants

Conditions

Temperature: 5 °C

Procedure

Triethylamine (3.9 mL, 27.9 mmol, 1.2 eq) was added to a suspension of 4-chloro-3-nitro[1,5]naphthyridine (4.87 g, 23.3 mmol, 1.0 eq) in dichloromethane (100 mL). The resulting solution was cooled to 5° C. and 4,4-diethoxybutylamine (5.36 mL, 27.9 mmol, 1.2 eq) was added dropwise over a period of 5 minutes. The reaction mixture was allowed to stir at ambient temperature for 2 hours and then diluted with saturated aqueous sodium bicarbonate (100 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (2×50 mL). The combined organics were dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to provide 7.93 g of (4,4-diethoxybutyl)(3-nitro[1,5]naphthyridin-4-yl)-amine as a red solid.

Workup

customThe phases were separated
extractionthe aqueous phase was extracted with dichloromethane (2×50 mL)
dry with materialThe combined organics were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3838744ebe5d4318bb66a1b52a165bf2
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778963B2

Reaction notes

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