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Sodium Iodide → 1-Benzyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide

HRID 1358926
ノート
印刷プレビュー

反応式

HRID 1358926 の反応式
C[O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][N:28]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[C:17]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:16][CH:15]=[C:14]([O:24][CH3:25])[C:12]=2[N:13]=1)=[O:7].[I-].[Na+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(#N)C.C(OCC)(=O)C>[CH3:25][O:24][C:14]1[C:12]2[N:13]=[C:9]([NH:8][C:6]([C:5]3[CH:26]=[CH:27][N:28]([CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:3](=[O:2])[CH:4]=3)=[O:7])[S:10][C:11]=2[C:17]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:16][CH:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 101942942-Methoxy-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide

生成物 1

HCID 102388211-Benzyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide収率 32%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 85 mg (0.21 mmol) 2-methoxy-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide in 2 ml acetonitrile were added 73 mg (0.43 mmol) sodium iodide and 0.05 ml (0.43 mmol) benzyl bromide. The mixture was heated at reflux for 16 h. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate, and washed sequentially with water and saturated brine. The organic phase was then dried over sodium sulfate and concentrated in vacuo. Flash chromatography (2/1 EtOAc/toluene) afforded 32 mg (32%) 1-benzyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide as a yellow crystalline solid. ES-MS m/e (%)): 499 (M+Na+, 14), 477 (M+H+, 100).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. washwashed sequentially with water and saturated brine
  4. dry with materialThe organic phase was then dried over sodium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-78fcdde4370c471ebe012be4a709bd22
出典データセット
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06599901B1

反応ノート

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