Triethylamine → 6-Chloro-7-[4-(4-naphthalen-1-yl-piperazin-1-yl)-butoxy]-3,4-dihydro-1H-[1,8]naphthyridin-2-one

HRID 1373606노트

반응식

HRID 1373606 반응식
[Cl: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.[C:20]1([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Cl: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:33]1[CH2:32][CH2:31][N:30]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)[CH2:35][CH2:34]1)[NH:6][C:7](=[O:12])[CH2:8][CH2:9]2

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 27373911-(1-Naphthyl)piperazine hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 210733394-(3-Chloro-7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde

생성물 1

HCID 210734526-Chloro-7-[4-(4-naphthalen-1-yl-piperazin-1-yl)-butoxy]-3,4-dihydro-1H-[1,8]naphthyridin-2-one수율 47%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of 4-(3-chloro-7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (400 mg, approx. 1.49 mmol, crude from previous reaction) in DCE (7 mL) was added 1-naphthalen-1-yl-piperazine hydrochloride (370 mg, 1.49 mmol) followed by Et3N (0.42 mL, 2.98 mmol). The solution was stirred for 15 min and NaBH(OAc)3 (410 mg, 1.94 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 (0–3% MeOH/CH2Cl2) afforded the title compound as an off-white foam (324 mg, 0.697 mmol, 47%). Et2O was added and the foam turned into a white solid after 5 minutes of stirring. The solid was collected by filtration, washed with Et2O and dried to give a white solid. MS: APCI: M+1: 465.2 (Exact Mass: 464.20).

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 (0–3% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-be62d2f27e614c08bcab73c37a7ab21c
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07160888B2

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