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 394145노트

반응식

HRID 394145 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 345198Adams' catalyst촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c068070b2483491d83e5ce28a95e482c
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809199B2

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