Ammonia → 437763-85-4

HRID 2229406Notes

Reaction equation

HRID 2229406 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][CH2:22][CH2:23][CH2:24][O:25]CC3C=CC=CC=3)[CH:16]=2)=[C:7]([NH:33][C:34]([NH:36][C:37]2[C:42]([CH:43]([CH3:45])[CH3:44])=[CH:41][C:40]([NH:46]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:39][C:38]=2[CH:66]([CH3:68])[CH3:67])=[O:35])[C:6]1=[O:69])[CH2:2][CH2:3][CH3:4].Cl.N>CC(C)=O.CO>[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][CH2:22][CH2:23][CH2:24][OH:25])[CH:16]=2)=[C:7]([NH:33][C:34]([NH:36][C:37]2[C:38]([CH:66]([CH3:68])[CH3:67])=[CH:39][C:40]([NH2:46])=[CH:41][C:42]=2[CH:43]([CH3:45])[CH3:44])=[O:35])[C:6]1=[O:69])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 18467164HCID 18467164, compound

Product 1

HCID 9938311437763-85-4Yield 90.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

To a solution of N-[1-butyl-4-[3-[3-(benzyloxy)propoxy]phenyl]-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N′-[2,6-diisopropyl-4-tritylaminophenyl]urea (1.60 g, 1.74 mmol) in a mixture of acetone (20 ml) and methanol (20 ml) is added conc. hydrochloric acid (1 ml, 12 mmol) under ice-cooling, and the mixture is stirred at room temperature for 14 hours. The reaction solution is made basic by adding thereto aqueous ammonia under ice-cooling, and extracted with ethyl acetate. The organic layer is washed twice with aqueous sodium hydrogen carbonate solution, and the solvent is concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give the title compound (1.07 g, 1.58 mmol).

Workup

  1. temperaturecooling
  2. additionby adding
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed twice with aqueous sodium hydrogen carbonate solution
  5. concentrationthe solvent is concentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3e413a698be64a42ae96f17ccdc1e98f
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

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