Sodium Hydroxide → HCID 58926731, compound

HRID 2378105Notes

Reaction equation

HRID 2378105 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[N:15]=2)[C:10](=O)[CH2:9][CH:8]1[CH2:19][CH3:20])=[O:6])([CH3:3])[CH3:2].[F:21][C:22]([F:36])([F:35])[C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:26][NH2:27].[BH4-].[Na+].[OH-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(OCC)(=O)C.CO>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[N:15]=2)[CH:10]([NH:27][CH2:26][C:25]2[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=[C:23]([C:22]([F:21])([F:35])[F:36])[CH:24]=2)[CH2:9][CH:8]1[CH2:19][CH3:20])=[O:6])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 4311764Sodium borohydrideHCID 58926727HCID 58926727, compound

Product 1

HCID 58926731HCID 58926731, compoundYield 89.8%

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Inject titanium(IV)isopropoxide (0.0870 ml, 0.299 mmol) to a mixture of 2-ethyl-7-methyl-4-oxo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid isopropyl ester (0.055 g, 0.199 mmol), and 3,5-bis(trifluoromethyl)benzylamine (0.0500 g, 0.199 mmol), and then stir at room temperature for 6 h. Add methanol (2 ml) followed by NaBH4 (0.0380 g, 0.995 mmol) and stir at room temperature overnight. Treat the mixture with 1 N sodium hydroxide (2 ml) and ethyl acetate (5 ml), and then filter through a Celite® pad. Wash the filtered residue thoroughly with ethyl acetate (30 ml). Separate the organic layer, wash with brine (3×50 ml), dry over sodium sulfate, filter, and concentrate to provide crude 4-(3,5-bis-trifluoromethyl-benzylamino)-2-ethyl-7-methyl-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid isopropyl ester (0.0900 g) which was elaborated without further purification. MS (ES+): 504 (M+H).

Workup

  1. stirringstir at room temperature overnight
  2. filtrationfilter through a Celite® pad
  3. washWash the filtered residue thoroughly with ethyl acetate (30 ml)
  4. customSeparate the organic layer
  5. washwash with brine (3×50 ml)
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-d353105ed8ec456780033acacdcda5f5
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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