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

HRID 1068003ノート

反応式

HRID 1068003 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 16073876N-[(4-chlorophenyl)methyl]-1-(2-ethylsulfanylethyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-94118e7b87a449688e80c0a1c478192c
出典データセット
uspto-grants-2001_06
特許番号
US06248739B1

反応ノート

読み込み中…