Diisopropylethylamine → (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-{4-[2-(2-methylphenoxy)ethyl]piperazinyl}propan-2-ol

HRID 271229ノート

反応式

HRID 271229 の反応式
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11].[CH3:12][C:13]1[S:14][C:15]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@H:24]([OH:32])[CH2:25][N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:18][C:16]=2[N:17]=1.CCN(C(C)C)C(C)C>CCO>[CH3:12][C:13]1[S:14][C:15]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@H:24]([OH:32])[CH2:25][N:26]3[CH2:27][CH2:28][N:29]([CH2:2][CH2:3][O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[CH3:11])[CH2:30][CH2:31]3)=[CH:18][C:16]=2[N:17]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 16225721-(2-Bromoethoxy)-2-methylbenzeneHCID 29943216(2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

生成物 1

HCID 11189927(2R)-1-(2-methylbenzothiazol-5-yloxy)-3-{4-[2-(2-methylphenoxy)ethyl]piperazinyl}propan-2-ol

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 2-bromo-1-(2-methylphenoxy)ethane (1.09 g, 5.09 mmol, crude) in EtOH (15 mL) was added (2R)-3-(2-methylbenzothiazol-5-yloxy)-1-piperazinylpropan-2-ol as prepared in Example 3A (250 mg, 0.81 mmol) and DIEA (1.5 mL, 8.6 mmol). The solution was stirred at reflux for 14 hours. Upon cooling, the solution was concentrated to an oil and then purified on an Isco™ (100% EtOAc hold 2 min, 8 min. gradient to 20% MeOH/EtOAc, hold 10 min) to afford (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-{4-[2-(2-methylphenoxy)ethyl]piperazinyl }propan-2-ol.

後処理

  1. temperatureat reflux for 14 hours
  2. temperatureUpon cooling
  3. concentrationthe solution was concentrated to an oil
  4. custompurified on an Isco™ (100% EtOAc hold 2 min, 8 min. gradient to 20% MeOH/EtOAc, hold 10 min)

出典と根拠

ORDレコード
ord-f90e95623ee14c17b61aff24c4efa443
出典データセット
uspto-grants-2008_11
特許番号
US07452889B2

反応ノート

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