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

HRID 2118356ノート

反応式

HRID 2118356 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-79e09a63e0304bd29e944f2ebdba3dd1
出典データセット
uspto-grants-2008_10
特許番号
US07442839B2

反応ノート

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