Triethylamine → HCID 21073531, compound

HRID 1373573Notes

Reaction equation

HRID 1373573 reaction equation
[CH3:1][C:2]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH2:14][C:13](=[O:19])[NH:12][C:11]=2[N:10]=1)([CH3:7])[CH2:3][CH2:4][CH:5]=O.Cl.[Cl:21][C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Cl:21][C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[N:29]1[CH2:34][CH2:33][N:32]([CH2:5][CH2:4][CH2:3][C:2]([CH3:7])([CH3:1])[O:8][C:9]2[N:10]=[C:11]3[C:16]([CH2:15][CH2:14][C:13](=[O:19])[NH:12]3)=[CH:17][CH:18]=2)[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochlorideHCID 21073408HCID 21073408, compound

Product 1

HCID 21073531HCID 21073531, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-methyl-4-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-pentanal (335 mg, crude) in DCE (6 mL) was added 2,3-dichlorophenyl-piperazine hydrochloride (335 mg, 1.25 mmol) followed by Et3N (0.35 mL, 2.50 mmol). The mixture was stirred for 10 min and then powdered NaBH(OAc)3 (365 mg, 1.72 mmol) was added. The reaction was stirred at room temperature for 2 h and then quenched with saturated NaHCO3. The mixture was extracted with EtOAc (2×). The organic layer was washed with saturated NaHCO3, H2O and brine, dried over Na2SO4 and concentrated. Purification by liquid chromatography (4% MeOH/CH2Cl2) gave the title compound as a white foam (395 mg, 0.827 mmol, 67% over 2 steps). The foam was dissolved in Et2O and 1 N HCl in Et2O (0.85 mL) was added. The resulting white precipitate was collected by filtration, washed with Et2O and dried to give a white solid (386 mg). MS: APCI: M+1: 477.1 (Exact Mass: 476.17).

Workup

  1. stirringThe reaction was stirred at room temperature for 2 h
  2. customquenched with saturated NaHCO3
  3. extractionThe mixture was extracted with EtOAc (2×)
  4. washThe organic layer was washed with saturated NaHCO3, H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by liquid chromatography (4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6d0f040432e94e8ba34a9b80be61054a
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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