Triethylamine → HCID 11654830, compound

HRID 1373566Notes

Reaction equation

HRID 1373566 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[CH:4]=[CH:3]1.Cl.[C:19]1([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[C:19]1([N:29]2[CH2:34][CH2:33][N:32]([CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:8]3[N:9]=[C:10]4[C:5]([CH:4]=[CH:3][C:2](=[O:1])[NH:11]4)=[CH:6][CH:7]=3)[CH2:31][CH2:30]2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27373911-(1-Naphthyl)piperazine hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 210733804-(7-Oxo-7,8-dihydro-1,8-naphthyridin-2-yloxy)butanal

Product 1

HCID 11654830HCID 11654830, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 4-(7-oxo-7,8-dihydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (175 mg, 0.754 mmol) and 1-naphthalen-1-yl-piperazine hydrochloride (206 mg, 0.829 mmol) in DCE (4 mL) was added Et3N (0.23 mL, 1.66 mmol). The mixture was stirred for 10 min and NaBH(OAc)3 (224 mg, 1.06 mmol) was added as a powder. The reaction was stirred at room temperature for 2 h and then quenched with saturated NaHCO3. The mixture was extracted with EtOAc. The organic layer was washed with saturated NaHCO3 and brine, dried over Na2SO4 and concentrated to give a white foam. Purification by liquid chromatography (5% MeOH/CH2Cl2) gave the title compound as a white foam (260 mg, 0.607 mmol, 80%). The foam was dissolved in a minimal amount of CH2Cl2 and Et2O was added. 1M HCl in Et2O (0.6 mL) was added and a white precipitate formed. The solid was collected by filtration, washed with Et2O and dried to give a white fluffy solid (257 mg). MS: APCI: M+1: 429.2 (Exact Mass: 428.22).

Workup

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

Sources & evidence

ORD record
ord-d92133a776584c5a9f8ac6bda9ff596a
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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