Dimethylformamide → tert-butyl [(1S)-2-{[1-(5-methoxy-1,3-benzothiazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate

HRID 2368073ノート

反応式

HRID 2368073 の反応式
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:5]=2[N:6]=1.[CH3:13][C@H:14]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:15][O:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(CC)C(C)C)(C)C.CN(C=O)C>O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([N:20]3[CH2:19][CH2:18][CH:17]([O:16][CH2:15][C@@H:14]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH3:13])[CH2:22][CH2:21]3)=[N:6][C:5]=2[CH:7]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 70592002-Chloro-5-methoxybenzothiazoleHCID 57517479tert-butyl [(1S)-1-methyl-2-(piperidin-4-yloxy)ethyl]carbamate

生成物 1

HCID 86658696tert-butyl [(1S)-2-{[1-(5-methoxy-1,3-benzothiazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate収率 64.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

A mixture of 2-chloro-5-methoxy-1,3-benzothiazole (143 mg), tert-butyl [(1S)-1-methyl-2-(piperidin-4-yloxy)ethyl]carbamate (186 mg), N,N-diisopropylethylamine (93 mg) and DMF (3 mL) was stirred at 150° C. for 1.5 hr under microwave irradiation. Water was added to the reaction mixture, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (194 mg).

後処理

  1. extractionthe obtained mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-834d1e909bc244d8a1daed8837beede2
出典データセット
uspto-grants-2014_04
特許番号
US08703758B2

反応ノート

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