Triphenylphosphine → N-[(4-chlorophenyl)methyl]-1-(2-ethylsulfanylethyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 1068003노트

반응식

HRID 1068003 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.C([CH:51](O)[CH2:52][S:53][CH2:54][CH:55](O)CC)C.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]([CH2:51][CH2:52][S:53][CH2:54][CH3:55])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 548436Sulfide, bis(2-hydroxybutyl)HCID 178522870HCID 178522870, 화합물

생성물 1

HCID 16073876N-[(4-chlorophenyl)methyl]-1-(2-ethylsulfanylethyl)-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 (393 mg), ethyl 2-hydroxyethylsulfide (0.16 mL) and diethyl azodicarboxylate (0.18 mL). The mixture is stirred at room temperature overnight 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 ethanolcyclohexane to afford 0.21 gm of the title compound as a white solid.

후처리

  1. customfrom Preparation No
  2. concentrationthen concentrated 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 ethanolcyclohexane

출처 및 근거

ORD 기록
ord-94118e7b87a449688e80c0a1c478192c
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248739B1

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