Acetone → HCID 22648204, compound

HRID 394149Notes

Reaction equation

HRID 394149 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:32])[N:13]2[C:24]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:31].[CH3:33][C:34]([CH3:36])=O.C([BH3-])#N.[Na+]>CO.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([CH:18]2[CH2:19][CH2:20][N:21]([CH:34]([CH3:36])[CH3:33])[CH2:22][CH2:23]2)[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:32])[N:13]2[C:24]1[C:25]([Cl:31])=[CH:26][CH:27]=[CH:28][C:29]=1[Cl:30]

Participants

7

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 22648056HCID 22648056, compound

Product 1

HCID 22648204HCID 22648204, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 14 mg of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-piperidin-4-yl-1,6-naphthyridin-2(1H)-one in 1 mL of MeOH was added 0.1 mL of acetone, then 9 mg of sodium cyanoborohydride. The mixture was stirred 5 h at rt, then diluted with 1 mL of EtOAc and 10 mL NaHCO3. The phases were separated and the aqueous phase was extracted with 2×10 mL of EtOAc. The combined organics were washed with 10 mL of brine, dried (Na2SO4), and concentrated. The residue was purified by preparative thin-layer chromatography, eluting with 95:5 CH2Cl2-2M NH3 in MeOH to yield the title compound. Mass spectrum (ESI) 528 (M+1). 1H NMR (500 MHz, CDCl3): selected peaks δ 1.07 (d, J=6.5 Hz, 6H), 1.71 (br s, 2H); 1.99 (br s, 2H); 2.26 (br s, 2H); 2.80 (br s, 2H); 3.02 (br s, 2H).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with 2×10 mL of EtOAc
  3. washThe combined organics were washed with 10 mL of brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by preparative thin-layer chromatography
  7. washeluting with 95:5 CH2Cl2-2M NH3 in MeOH

Sources & evidence

ORD record
ord-39ab21c08400465daaab5cf31c649360
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

Loading…