Triethylamine → HCID 9886058, compound

HRID 479861Notes

Reaction equation

HRID 479861 reaction equation
[N:1]1([C:6]2[N:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH:11]=[C:10]([C:16]([OH:18])=O)[C:9]3=[O:19])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.ClC(OCC)=O.[CH3:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1>O.CN(C)C=O.O1CCCC1>[CH3:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH:40][C:16]([C:10]2[C:9](=[O:19])[C:8]3[C:13](=[CH:14][CH:15]=[C:6]([N:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[N:7]=3)[NH:12][CH:11]=2)=[O:18])=[CH:37][CH:36]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 754524-MethoxybenzylamineHCID 13344378HCID 13344378, compound

Product 1

HCID 9886058HCID 9886058, compoundYield 60.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-pyrrolidino-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid (80 mg, 0.3 mmol) and triethylamine (0.11 mL, 0.8 mmol) in 5:1 tetrahydrofuran: N,N-dimethylformamide (6 mL) at 0° C. was added ethyl chloroformate (0.09 mL, 0.9 mmol). After stirring at 0° C. for 0.5 h, 4-methoxybenzylamine (0.1 mL, 0.8 mmol) was added. The reaction mixture was allowed to ambient temperature and stirred for 0.5 h. Water was added and the resulting precipitate collected, washed with water and ether and dried. The solid was combined with 1N NaOH (5 mL) and ethanol (2 mL) and heated at reflux for 0.25 h. The reaction mixture was cooled in an ice bath, 3N HCl was added to achieve pH 8, and the precipitate collected, rinsed with water and ether and dried to give 69 mg of N-(4-methoxybenzyl) 6-pyrrolidino-4-oxo-1,4-dihydro-1,5-naphthyri-dine-3-carboxamide; m.p. 270-272 C. Compound 8.

Workup

  1. customwas allowed to ambient temperature
  2. stirringstirred for 0.5 h
  3. customthe resulting precipitate collected
  4. washwashed with water and ether
  5. customdried
  6. temperatureheated
  7. temperatureat reflux for 0.25 h
  8. temperatureThe reaction mixture was cooled in an ice bath
  9. addition3N HCl was added
  10. customthe precipitate collected
  11. washrinsed with water and ether
  12. customdried

Sources & evidence

ORD record
ord-162c232e86264b7eaea90931d77b381c
Source dataset
uspto-grants-2003_11
Patent number
US06646124B2

Reaction notes

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