Triethylamine → HCID 9808762, compound

HRID 2229391Notes

Reaction equation

HRID 2229391 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7](C(O)=O)[C:6]1=[O:26])[CH2:2][CH2:3][CH3:4].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])=CC=1.C([N:46]([CH2:49]C)CC)C.[C:51]([C:55]1[CH:61]=[CH:60][C:59]([CH2:62][N:63]2[CH2:68][CH2:67][O:66][CH2:65][CH2:64]2)=[CH:58][C:56]=1[NH2:57])([CH3:54])([CH3:53])[CH3:52]>CN(C=O)C.O>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7]([NH:46][C:49]([NH:57][C:56]2[CH:58]=[C:59]([CH2:62][N:63]3[CH2:68][CH2:67][O:66][CH2:65][CH2:64]3)[CH:60]=[CH:61][C:55]=2[C:51]([CH3:54])([CH3:52])[CH3:53])=[O:34])[C:6]1=[O:26])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 15485011HCID 15485011, compoundHCID 15485012HCID 15485012, compound

Product 1

HCID 9808762HCID 9808762, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-butyl-3-carboxy-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine (2.0 g, 5.60 mmol) in DMF (N,N-dimethylformamide, 20 ml) are added DPPA (diphenyl phosphorylazide, 1.87 g, 6.81 mmol) and triethylamine (0.57 g, 5.68 mmol), and the mixture is stirred at room temperature for one hour, and stirred at about 60° C. for 3 hours. To the mixture is added 2-tert-butyl-5-(morpholinomethyl)aniline (1.69 g, 6.81 mmol), and the mixture is stirred at 50-60° C. for 12 hours. To the reaction solution is added water, and the mixture is extracted with ethyl acetate. The extract is washed with water and a saturated brine, and dried over anhydrous magnesium sulfate. The solvent is evaporated under reduced pressure, and the resulting residue is purified by silica gel column chromatography (chloroform to 2% methanol/chloroform) to give the title compound (3.06 g, 5.12 mmol) as colorless oil.

Workup

  1. stirringstirred at about 60° C. for 3 hours
  2. stirringthe mixture is stirred at 50-60° C. for 12 hours
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe extract is washed with water
  5. dry with materiala saturated brine, and dried over anhydrous magnesium sulfate
  6. customThe solvent is evaporated under reduced pressure
  7. customthe resulting residue is purified by silica gel column chromatography (chloroform to 2% methanol/chloroform)

Sources & evidence

ORD record
ord-2259b59c1b5b44c7b21c62ee2c0e8d5e
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

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