Triethylamine → HCID 69507092, compound

Participants

Reaction Conditions

Reaction Steps

The preparation of 4-chloro-3-nitro[1,5]naphthyridine is described in Part A of Example 1. Ethyl 4-aminobutyrate hydrochloride (9.6 g, 57.3 mmol, 1.2 eq) was added to a suspension of 4-chloro-3-nitro[1,5]naphthyridine (10.0 g, 47.7 mmol, 1.0 eq) in dichloromethane (200 mL) and stirred at 5° C. Triethylamine (16.6 mL, 119.3 mmol, 2.5 eq) was added and the reaction mixture was stirred for 2 hours and allowed to warm to ambient temperature. The mixture was diluted with dichloromethane (200 mL) and washed with saturated aqueous sodium bicarbonate (2×150 mL). The phases were separated and the combined aqueous layers were extracted with chloroform (100 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 14.5 g of ethyl 4-[(3-nitro[1,5]naphthyridinyl)amino]butyrate as a yellow solid.

Provenance & Evidence