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

HRID 624227

반응식

HRID 624227 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cebf238a35b74ebcad8abec2965ad3a0
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302989B2

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