Triethylamine → 6-Bromo-7-{4-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-butoxy}-3,4-dihydro-1H-[1,8]naphthyridin-2-one

HRID 1373607

반응식

HRID 1373607 반응식
[Br:1][C:2]1[C:3]([O:13][CH2:14][CH2:15][CH2:16][CH:17]=O)=[N:4][C:5]2[NH:6][C:7](=[O:12])[CH2:8][CH2:9][C:10]=2[CH:11]=1.Cl.[Cl:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5](=[N:4][C:3]=1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][N:31]1[CH2:30][CH2:29][N:28]([C:22]3[CH:23]=[CH:24][CH:25]=[C:26]([Cl:27])[C:21]=3[Cl:20])[CH2:33][CH2:32]1)[NH:6][C:7](=[O:12])[CH2:8][CH2:9]2

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochlorideHCID 210733374-(3-Bromo-7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde

생성물 1

HCID 210734496-Bromo-7-{4-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-butoxy}-3,4-dihydro-1H-[1,8]naphthyridin-2-one수율 69%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of 4-(3-bromo-7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (0.43 g, approx. 1.37 mmol, crude from previous reaction) in DCE (6 mL) was added 1-(2,3-dichloro-phenyl)-piperazine hydrochloride (367 mg, 1.37 mmol) followed by Et3N (0.38 mL, 2.75 mmol). The solution was stirred for 15 min and NaBH(OAc)3 (407 mg, 1.92 mmol) was added as a powder. The reaction was stirred at room temperature for 2 h and quenched with saturated NaHCO3 and H2O. The mixture was extracted with EtOAc. The organic layer was washed with saturated NaHCO3, H2O and brine, dried over Na2SO4 and concentrated. Purification by liquid chromatography (4% MeOH/CH2Cl2) afforded the title compound as a white foam (497 mg, 0.941 mmol, 69%). MS: APCI: M+1: 527.0, 529.0, 531.0 (Exact Mass: 526.05).

후처리

  1. stirringThe reaction was stirred at room temperature for 2 h
  2. customquenched with saturated NaHCO3 and H2O
  3. extractionThe mixture was extracted with EtOAc
  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)

출처 및 근거

ORD 기록
ord-1115c5de1d7b4589aa496c4cadd82c31
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07160888B2

연결된 노트

불러오는 중…