Triethylamine → HCID 69506714, compound

HRID 2366691Notes

Reaction equation

HRID 2366691 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.[NH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(N(CC)CC)C>ClCCl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 126496614-Aminobutyrate ethyl hydrochlorideHCID 131227874-Chloro-3-nitro-1,5-naphthyridine

Product 1

HCID 69506714HCID 69506714, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

A suspension of 4-chloro-3-nitro[1,5]naphthyridine (10.0 g, 47.7 mmol) and ethyl 4-aminobutyrate hydrochloride (9.6 g, 57 mmol) in dichloromethane (200 mL) was cooled to 5° C. Triethylamine (16.6 mL, 119 mmol) was added, and the reaction was allowed to warm to ambient temperature and stirred for two hours. The mixture was diluted with dichloromethane (200 mL) and washed with saturated aqueous sodium bicarbonate (2×150 mL). The combined aqueous fractions were extracted with dichloromethane (100 mL), and the combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 14.5 g of ethyl 4-(3-nitro[1,5]naphthyridin-4-ylamino)butanoate as a yellow solid.

Workup

  1. temperatureto warm to ambient temperature
  2. washwashed with saturated aqueous sodium bicarbonate (2×150 mL)
  3. extractionThe combined aqueous fractions were extracted with dichloromethane (100 mL)
  4. dry with materialthe combined organic fractions were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cbbbd970080d40cb80408bfe7dc28fc0
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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