Diisopropylethylamine → 5-{(1R)-2-[[6-({4-[3-(Cyclopentylsulfonyl)phenyl]butyl}oxy)hexyl](phenylmethyl)amino]-1-hydroxyethyl}-8-[(Phenylmethyl)oxy]-2(1H)-quinolinone

HRID 2118356노트

반응식

HRID 2118356 반응식
[CH2:1]([NH:8][CH2:9][C@@H:10]([C:12]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:30])[NH:17]2)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Br[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][CH2:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[C:54]([S:58]([CH:61]2[CH2:65][CH2:64][CH2:63][CH2:62]2)(=[O:60])=[O:59])[CH:53]=1>CC#N.O>[CH:61]1([S:58]([C:54]2[CH:53]=[C:52]([CH2:51][CH2:50][CH2:49][CH2:48][O:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][C@@H:10]([C:12]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[C:18]4[C:13]=3[CH:14]=[CH:15][C:16](=[O:30])[NH:17]4)[OH:11])[CH:57]=[CH:56][CH:55]=2)(=[O:60])=[O:59])[CH2:65][CH2:64][CH2:63][CH2:62]1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 691197205-[(1R)-2-(Benzylamino)-1-hydroxyethyl]-8-(benzyloxy)quinolin-2(1H)-oneHCID 691198271-{4-[(6-Bromohexyl)oxy]butyl}-3-(cyclopentylsulfonyl)benzene

생성물 1

HCID 692041025-{(1R)-2-[[6-({4-[3-(Cyclopentylsulfonyl)phenyl]butyl}oxy)hexyl](phenylmethyl)amino]-1-hydroxyethyl}-8-[(Phenylmethyl)oxy]-2(1H)-quinolinone수율 25.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

5-[(1R)-2-(Benzylamino)-1-hydroxyethyl]-8-(benzyloxy)quinolin-2(1H)-one (40 mg) was dissolved in MeCN (2 ml). N,N,-diisopropylethylamine (0.03 ml) and 1-{4-[(6-bromohexyl)oxy]butyl}-3-(cyclopentylsulfonyl)benzene (Example 1v) (30 mg) were added and the reaction mixture was heated at 80° under nitrogen for 48 h. The mixture was then diluted with water and extracted with EtOAc. The organic phases were combined, dried (MgSO4), and evaporated in vacuo. The residue was purified on a silica SPE bond elut cartridge, eluting with EtOAc-cyclohexane mixtures, to give the title compound, (13 mg)

후처리

  1. temperaturethe reaction mixture was heated at 80° under nitrogen for 48 h
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was purified on a silica SPE bond elut cartridge
  6. washeluting with EtOAc-cyclohexane mixtures

출처 및 근거

ORD 기록
ord-79e09a63e0304bd29e944f2ebdba3dd1
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442839B2

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