N-Methylphenylethanolamine → N-(4-Chlorobenzyl)-6-{[(2-hydroxy-2-phenylethyl)(methyl)-amino]methyl}-1-methyl-4-oxo-1,4-dihydro-3quinolinecarboxamide

HRID 1068006

반응식

HRID 1068006 반응식
[Cl:1][C:2]1[CH:25]=[CH:24][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]Cl)[CH:17]=3)[N:12]([CH3:23])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:35][NH:36][CH2:37][CH:38]([OH:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:3]=[CH:4][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:36]([CH2:37][CH:38]([OH:45])[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH3:35])[CH:17]=3)[N:12]([CH3:23])[CH:11]=2)=[O:9])=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 913N-MethylphenylethanolamineHCID 81531DiisopropylethylamineHCID 21192571N-(4-Chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

생성물 1

HCID 21192531N-(4-Chlorobenzyl)-6-{[(2-hydroxy-2-phenylethyl)(methyl)-amino]methyl}-1-methyl-4-oxo-1,4-dihydro-3quinolinecarboxamide수율 63.8%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A solution of N-(4-chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.06 gm) from Preparation No. 35 in dry NMP (2 mL) containing diisopropylethylarnine (0.04 mL) is treated with α-(methylaminomethyl)-benzyl alcohol (0.04 gm). The reaction mixture is shaken at room temperature for 3 days then concentrated under reduced pressure. The residue is partioned between dichloromethane and water. The separated organic layer is washed with two additional portions of water, brine, dried (Na2SO4) and concentrated under reduced pressure. The residue is adsorbed onto silica and purified by flash column chromatography eluting with 2% to 6% methanol in dichloromethane and then by recrystallization from ethyl acetate-hexanes to afford 0.05 gm of the title compound as a white solid.

후처리

  1. concentrationthen concentrated under reduced pressure
  2. washThe separated organic layer is washed with two additional portions of water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash column chromatography
  6. washeluting with 2% to 6% methanol in dichloromethane
  7. customby recrystallization from ethyl acetate-hexanes

출처 및 근거

ORD 기록
ord-69358d5342f5415e8d81080eb6212e47
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248739B1

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