Triethylamine → HCID 21073534, compound

HRID 1373599Notes

Reaction equation

HRID 1373599 reaction equation
[CH3:1][C:2]1([CH3:20])[C:11](=[O:12])[NH:10][C:9]2[N:8]=[C:7]([O:13][CH2:14][CH2:15][CH2:16][CH:17]=O)[CH:6]=[CH:5][C:4]=2[C:3]1=[O:19].Cl.[Cl:22][C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Cl:22][C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[N:30]1[CH2:35][CH2:34][N:33]([CH2:17][CH2:16][CH2:15][CH2:14][O:13][C:7]2[N:8]=[C:9]3[C:4]([C:3](=[O:19])[C:2]([CH3:20])([CH3:1])[C:11](=[O:12])[NH:10]3)=[CH:5][CH:6]=2)[CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochlorideHCID 21073359HCID 21073359, compound

Product 1

HCID 21073534HCID 21073534, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-(6,6-dimethyl-5,7-dioxo-5, 6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (0.520 g, 1.88 mmol) in DCE (6 mL) was added 1-(2,3-dichloro-phenyl)-piperazine hydrochloride (0.503 g, 1.88 mmol) followed by Et3N (0.53 mL, 3.76 mmol). The mixture was stirred for 20 minutes at room temperature and NaBH(OAc)3 (0.56 g, 2.60 mmol) was added. The reaction was stirred for 2.5 h and quenched with saturated NaHCO3 and water. The mixture was extracted with EtOAc and the organic layer was washed with saturated NaHCO3, water and brine, dried over Na2SO4 and concentrated. Purification by liquid chromatography on silica gel (0–5% MeOH/CH2Cl2) gave a white solid (0.277 g, 0.564 mmol, 30%). MS: APCI: M+1: 491.1 (Exact Mass: 490.15).

Workup

  1. stirringThe reaction was stirred for 2.5 h
  2. customquenched with saturated NaHCO3 and water
  3. extractionThe mixture was extracted with EtOAc
  4. washthe organic layer was washed with saturated NaHCO3, water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by liquid chromatography on silica gel (0–5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-868c6196be124bbb8fd6108c5015cfc3
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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