Benzoyl isothiocyanate → 1-Benzoyl-3-[3-iodo-5-methoxy-2-(tetrahydro-pyran-4-yl)-pyridin-4-yl]-thiourea

HRID 917474

反応式

HRID 917474 の反応式
[I:1][C:2]1[C:3]([CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:4][CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[NH2:8].[C:17]([N:25]=[C:26]=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[C:17]([NH:25][C:26]([NH:8][C:7]1[C:6]([O:9][CH3:10])=[CH:5][N:4]=[C:3]([CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:2]=1[I:1])=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

4

反応物 2

HCID 68284Benzoyl isothiocyanateHCID 589626993-Iodo-5-methoxy-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine

生成物 1

HCID 589627041-Benzoyl-3-[3-iodo-5-methoxy-2-(tetrahydro-pyran-4-yl)-pyridin-4-yl]-thiourea収率 80.4%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a stirred solution of 725 mg (2.17 mmol) 3-iodo-5-methoxy-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine in 14 ml acetone was added dropwise 0.35 ml (2.60 mmol) benzoyl isothiocyanate at room temperature. The reaction mixture then heated at reflux for 2 h before being cooled to room temperature concentrated in vacuo. Flash chromatography (ethyl acetate/heptane) afforded 868 mg (80%) 1-benzoyl-3-[3-iodo-5-methoxy-2-(tetrahydro-pyran-4-yl)-pyridin-4-yl]-thiourea as a white crystalline solid. ES-MS m/e (%): 498 (M+H+, 100).

後処理

  1. temperatureThe reaction mixture then heated
  2. temperatureat reflux for 2 h
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4482ad14923b45e7912d0986f40bb899
出典データセット
uspto-grants-2007_09
特許番号
US07273865B2

関連ノート

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