Triethylamine → HCID 11662306, compound

HRID 1373555Notes

Reaction equation

HRID 1373555 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.[Cl:19][C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[Cl:19][C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[N:27]1[CH2:32][CH2:31][N:30]([CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:8]2[N:9]=[C:10]3[C:5]([CH:4]=[CH:3][C:2](=[O:1])[NH:11]3)=[CH:6][CH:7]=2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochlorideHCID 210733804-(7-Oxo-7,8-dihydro-1,8-naphthyridin-2-yloxy)butanal

Product 1

HCID 11662306HCID 11662306, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 4-(7-oxo-7,8-dihydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (crude from previous reaction) in dichloroethane (6 mL) was added 2,3-dichlorophenylpiperazine hydrochloride (321 mg, 1.20 mmol) followed by Et3N (0.34 mL, 2.40 mmol, 2 equiv). The resulting suspension was stirred for 5 min and NaBH(OAc)3 (356 mg, 1.68 mmol, 1.4 equiv) was added as a powder. The reaction was stirred at room temperature for 2 h. The reaction was quenched with saturated NaHCO3 and H2O and the mixture was extracted with EtOAc. The organic layer was washed with saturated NaHCO3 and brine, dried over Na2SO4 and concentrated. Purification by liquid chromatography (4–5% MeOH/CH2Cl2) gave the title compound as a white foam (378 mg, 0.845 mmol, 70% over 2 steps). The foam was dissolved in Et2O/CH2Cl2 and 1 N HCl in Et2O (0.82 mL) was added. The resulting white precipitate was collected by filtration, washed with Et2O and dried to give a white solid (355 mg). MS: APCI: M+1: 447.1 (Exact Mass: 446.13).

Workup

  1. stirringThe reaction was stirred at room temperature for 2 h
  2. customThe reaction was quenched with saturated NaHCO3 and H2O
  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. customPurification by liquid chromatography (4–5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-73652b15502c42b4921bded231c9b414
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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