Acetic Acid → Methyl 2-(4-(pyridin-3-yl)benzylamino)thiazole-5-carboxylate

HRID 624227

反応式

HRID 624227 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH:2]=1.[NH2:15][C:16]1[S:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=1.C(O)(=O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH:15][C:16]3[S:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=3)=[CH:9][CH:8]=2)[CH:2]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 238005Methyl 2-aminothiazole-5-carboxylateHCID 36930464-(Pyridin-3-yl)benzaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 86665086Methyl 2-(4-(pyridin-3-yl)benzylamino)thiazole-5-carboxylate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

In a 250 mL round-bottomed flask was added 4-(pyridin-3-yl)benzaldehyde (4 g, 21.83 mmol), methyl 2-aminothiazole-5-carboxylate (3.45 g, 21.83 mmol), and acetic acid (0.375 ml, 6.55 mmol) in toluene (109 ml). The mixture was heated at reflux under Dean-Stark conditions for 3 hours, cooled, concentrated and redissolved in methanol. The mixture was cooled to 0° C. and sodium borohydride (1.322 g, 34.9 mmol) was carefully added. The mixture was warmed to room temperature and the resulting suspension was filtered with water washes to provide the title compound after drying.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux under Dean-Stark conditions for 3 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. dissolutionredissolved in methanol
  6. temperatureThe mixture was warmed to room temperature
  7. filtrationthe resulting suspension was filtered with water

出典と根拠

ORDレコード
ord-cebf238a35b74ebcad8abec2965ad3a0
出典データセット
uspto-grants-2016_04
特許番号
US09302989B2

関連ノート

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