Triethylamine → HCID 69506747, compound

HRID 2366712Notes

Reaction equation

HRID 2366712 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][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(N(CC)CC)C>C(Cl)(Cl)Cl>[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][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 458476ethyl 6-aminohexanoate hydrochlorideHCID 131227874-Chloro-3-nitro-1,5-naphthyridine

Product 1

HCID 69506747HCID 69506747, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 4-chloro-3-nitro[1,5]naphthyridine (9.0 g, 42.9 mmol) in chloroform (180 mL) was cooled to approximately 0° C. Ethyl 6-aminohexanoate hydrochloride (12.6 g, 64.4 mmol) and triethylamine (16.6 mL, 119 mmol) were sequentially added with stirring, and the reaction was stirred for 15 minutes. The mixture was diluted with chloroform (180 mL), washed with 1% aqueous sodium carbonate (3×125 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide ethyl 6-(3-nitro[1,5]naphthyridin-4-ylamino)hexanoate as a yellow oil.

Workup

  1. stirringthe reaction was stirred for 15 minutes
  2. washwashed with 1% aqueous sodium carbonate (3×125 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-260bfe37ee4c43ff9cbfaa0af57ab2eb
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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