Triphenylphosphine → N-[(4-chlorophenyl)methyl]-1-(3-methylsulfanylpropyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 1068004노트

반응식

HRID 1068004 반응식
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:49][C:50]1C=[CH:53][S:52][C:51]=1CCCO.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[CH:17]=3)[N:12]([CH2:49][CH2:50][CH2:51][S:52][CH3:53])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 552672123-(3-Methylthiophen-2-yl)propan-1-olHCID 178522870HCID 178522870, 화합물

생성물 1

HCID 16073877N-[(4-chlorophenyl)methyl]-1-(3-methylsulfanylpropyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A dry flask containing N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (0.20 gm) from Preparation No. 40 in dry THF (5 mL) under an argon atmosphere is added triphenylphosphine (396 mg), 3-methylthiolpropanol (0.16 mL) and diethyl azodicarboxylate (0.18 mL). The mixture is stirred at room temperature 48 hours and then concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 2% to 6% methanol in dichloromethane and then by recrystallization from toluene-cyclohexane to afford 0.14 gm of the title compound as a white solid.

후처리

  1. customfrom Preparation No
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product is purified by flash column chromatography
  4. washeluting with 2% to 6% methanol in dichloromethane
  5. customby recrystallization from toluene-cyclohexane

출처 및 근거

ORD 기록
ord-f8182ebc98574269b34f79674938c7af
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248739B1

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