Piperazine → HCID 21073628, compound

HRID 1373632Notes

Reaction equation

HRID 1373632 reaction equation
[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

Participants

10

Reactant 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

Product 1

HCID 21073628HCID 21073628, compoundYield 64%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-619b719d568c4b0aa46383d7539ac240
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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