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

HRID 1068005ノート

反応式

HRID 1068005 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:49](O)#[C:50][CH2:51][CH2:52][OH:53].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][C:50]#[C:51][CH2:52][OH:53])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 13931173Butyne-1,4-diolHCID 178522870HCID 178522870、化合物

生成物 1

HCID 16073878N-[(4-chlorophenyl)methyl]-1-(4-hydroxybut-2-ynyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide収率 68.7%

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), 1,4-butyne diol (0.45 gm) and diethyl azodicarboxylate (0.18 mL). The mixture is stirred at room temperature overnight, concentrated under reduced pressure and adsorbed onto silica gel. The crude product is purified by flash column chromatography eluting with 2% to 6% methanol in dichloromethane and then by recrystallization from methanol-acetonitrile to afford 0.16 gm of the title compound as a white solid.

後処理

  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 methanol-acetonitrile

出典と根拠

ORDレコード
ord-0b23e5cb114f4624836a2e02a5f615ba
出典データセット
uspto-grants-2001_06
特許番号
US06248739B1

反応ノート

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