1-Tert-butyl-4-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl]-1,2,3,6-tetrahydropyridinium chloride → 7-(1-tert-butylpiperidin-4-yl)-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

HRID 394145Notes

Reaction equation

HRID 394145 reaction equation
[Cl-].[C:2]([NH+:6]1[CH2:11][CH:10]=[C:9]([C:12]2[CH:21]=[C:20]3[C:15]([CH:16]=[CH:17][C:18](=[O:30])[N:19]3[C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])=[C:14]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])[N:13]=2)[CH2:8][CH2:7]1)([CH3:5])([CH3:4])[CH3:3]>CO.CCOC(C)=O.O=[Pt]=O>[C:2]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[CH:21]=[C:20]3[C:15]([CH:16]=[CH:17][C:18](=[O:30])[N:19]3[C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])=[C:14]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])[N:13]=2)[CH2:10][CH2:11]1)([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 1

HCID 698603931-Tert-butyl-4-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl]-1,2,3,6-tetrahydropyridinium chloride

Product 1

HCID 226481157-(1-tert-butylpiperidin-4-yl)-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 75 mg of 1-tert-butyl-4-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl]-1,2,3,6-tetrahydropyridinium chloride in 3 mL of MeOH and 1 mL of EtOAc was added 35 mg of PtO2 (Adam's catalyst). The mixture was evacuated and purged with N2, then evacuated and purged with H2, then stirred under an H2 balloon for 1 h. The mixture was filtered through Celite, washing with MeOH, and concentrated. The residue was purified by preparative thin-layer chromatography, eluting with 95:5 CH2Cl2-2M NH3 in MeOH, followed by preparative HPLC (YMC C8 19×50 mm column; 10:90 to 90:10 v/v acetonitrile/water+0.05% TFA over 12 min; 20 mL/minute) to yield the title compound. Mass spectrum (ESI) 542 (M+1). 1H NMR (500 MHz, CD3OD): δ 1.40 (s, 9H); 2.04-2.20 (m, 4H); 3.00-3.12 (m, 3H); 3.68 (br d, J=12.5 Hz, 2H); □6.46 (s, 1H); 6.75 (d, J=10 Hz, 1H); 7.48-7.75 (m, 8H).

Workup

  1. customThe mixture was evacuated
  2. custompurged with N2
  3. customevacuated
  4. custompurged with H2
  5. filtrationThe mixture was filtered through Celite
  6. washwashing with MeOH
  7. concentrationconcentrated
  8. customThe residue was purified by preparative thin-layer chromatography
  9. washeluting with 95:5 CH2Cl2-2M NH3 in MeOH
  10. customfollowed by preparative HPLC (YMC C8 19×50 mm column; 10:90 to 90:10 v/v acetonitrile/water+0.05% TFA over 12 min; 20 mL/minute)

Sources & evidence

ORD record
ord-c068070b2483491d83e5ce28a95e482c
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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