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Acetic Acid → 1-{1-[(5-Chlorothiophen-2-yl)methyl]piperidin-4-yl}-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one

HRID 1506242
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HRID 1506242 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]4[N:19]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[CH:17][C:15]4=3)[C:10](=[O:28])[CH:9]=[CH:8]2)[CH2:3][CH2:2]1.[Cl:29][C:30]1[S:34][C:33]([CH:35]=O)=[CH:32][CH:31]=1.B.N1C=CC=CC=1C.C(O)(=O)C>CO>[Cl:29][C:30]1[S:34][C:33]([CH2:35][N:1]2[CH2:6][CH2:5][CH:4]([N:7]3[C:16]4[C:11](=[CH:12][N:13]=[C:14]5[N:19]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:27])[CH3:26])[CH:18]=[CH:17][C:15]5=4)[C:10](=[O:28])[CH:9]=[CH:8]3)[CH2:3][CH2:2]2)=[CH:32][CH:31]=1
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참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 817002-Thiophenecarboxaldehyde, 5-chloro-HCID 16217944Borane;2-methylpyridineHCID 712582261-(Piperidin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one

생성물 1

HCID 867266401-{1-[(5-Chlorothiophen-2-yl)methyl]piperidin-4-yl}-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one
수율 75.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

1-(Piperidin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one (20 mg, 0.050 mmol) in methanol was stirred with 5-chlorothiophen-2-carbaldehyde (6.3 μL, 0.06 mmol), 2-picoline borane (6.4 mg, 0.06 mmol) and acetic acid (100 μL) for one day. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=10/1 (v/v)) to give the title compound as a colorless oil (20 mg, yield 75%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform/methanol=10/1 (v/v))

출처 및 근거

ORD 기록
ord-81aac1c10a2a465eaf9c320de049c5ee
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09216999B2

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