Piperazine → HCID 21073628, 화합물

HRID 1373632노트

반응식

HRID 1373632 반응식
[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15][CH:16]=O)[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[N:18]1([C:24]2[C:32]3[O:31][C:30](=[O:33])[NH:29][C:28]=3[CH:27]=[CH:26][CH:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.N1CCNCC1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(Cl)Cl.CO.CCOCC.CN(C=O)C>[O:33]=[C:30]1[NH:29][C:28]2[CH:27]=[CH:26][CH:25]=[C:24]([N:18]3[CH2:23][CH2:22][N:21]([CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:8]4[N:9]=[C:10]5[C:5]([CH2:4][CH2:3][C:2](=[O:1])[NH:11]5)=[CH:6][CH:7]=4)[CH2:20][CH2:19]3)[C:32]=2[O:31]1

참가 물질

10

반응물 5

HCID 4837PiperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 206446407-(Piperazin-1-yl)-benzoxazol-2(3H)-oneHCID 210733774-((7-Oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)oxy)butanal

생성물 1

HCID 21073628HCID 21073628, 화합물수율 64%

시약·촉매·용매 4

HCID 111,2-Dichloroethane용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매HCID 21226129Dichloromethane methanol용매

실험 절차

To a solution of 4-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (300 mg, 1.28 mmol) in DCE (6 mL) was added 7-piperazin-1-yl-3H-benzooxazol-2-one (309 mg, 1.41 mmol, prepared according to EP 0189612 and/or EP 0138280; Drugs of the Future, 2001, 26,128). The piperazine did not dissolve so DMF (1 mL) was added. The reaction was stirred for 10 min and NaBH(OAc)3 (380 mg, 1.79 mmol) was added. The reaction was stirred for 2 h at RT. Saturated NaHCO3 was added and the mixture was extracted with EtOAc (along with a little MeOH). The organic layer was washed with H2O and brine, and concentrated to give a light brown solid. The solid was dissolved in CH2Cl2/MeOH, absorbed onto SiO2 and purified by liquid chromatography (AnaLogix, RS-40, 0–5% MeOH/CH2Cl2) to give a white solid. Et2O was added and the solid was collected by filtration and dried to give the product as a white solid (360 mg, 0.823 mmol, 64%). MS: APCI: M+1: 438.2 (Exact Mass: 437.21).

후처리

  1. customprepared
  2. additionwas added
  3. stirringThe reaction was stirred for 2 h at RT
  4. extractionthe mixture was extracted with EtOAc (along with a little MeOH)
  5. washThe organic layer was washed with H2O and brine
  6. concentrationconcentrated
  7. customto give a light brown solid
  8. customabsorbed onto SiO2
  9. custompurified by liquid chromatography (AnaLogix, RS-40, 0–5% MeOH/CH2Cl2)
  10. customto give a white solid
  11. filtrationthe solid was collected by filtration
  12. customdried

출처 및 근거

ORD 기록
ord-619b719d568c4b0aa46383d7539ac240
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07160888B2

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