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

HRID 522697

반응식

HRID 522697 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

실험 절차

To a 250 mL round-bottomed flask was added 4-(pyridin-3-yl)benzaldehyde (4 g, 21.8 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 reaction mixture was heated at reflux under Dean-Stark conditions for 3 hours, cooled to room temperature, and the volatiles were removed by rotary evaporation. Methanol was added, the solution was cooled to 0° C., and sodium borohydride (1.322 g, 34.9 mmol) was carefully added. The reaction was stirred at 0° C. for 15 minutes and allowed to warm to room temperature while stirring for an additional 2 hour. The solids were filtered off, washed with water and dried under high vacuum to give the title compound which was used in the next step without further purification.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under Dean-Stark conditions for 3 hours
  3. customthe volatiles were removed by rotary evaporation
  4. additionMethanol was added
  5. temperaturethe solution was cooled to 0° C.
  6. temperatureto warm to room temperature
  7. stirringwhile stirring for an additional 2 hour
  8. filtrationThe solids were filtered off
  9. washwashed with water
  10. customdried under high vacuum

출처 및 근거

ORD 기록
ord-c66c9fb567dc416e8910a24320d80ad9
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334264B2

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