Dimethylformamide → N-(4-fluorobenzyl)-5-isocyanato-N-(4-(pyridin-3-yl)benzyl)thiazol-2-amine

HRID 624229노트

반응식

HRID 624229 반응식
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:19][CH:18]=2)[C:8]2[S:9][C:10](C(O)=O)=[CH:11][N:12]=2)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.C[N:38](C)[CH:39]=[O:40].C[Si](N=[N+]=[N-])(C)C>ClCCl>[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:21][CH:22]=2)[C:8]2[S:9][C:10]([N:38]=[C:39]=[O:40])=[CH:11][N:12]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 78378AzidotrimethylsilaneHCID 687536802-((4-Fluorobenzyl)(4-(pyridin-3-yl)benzyl)amino)thiazole-5-carboxylic acid

생성물 1

HCID 86665087N-(4-fluorobenzyl)-5-isocyanato-N-(4-(pyridin-3-yl)benzyl)thiazol-2-amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a 50 mL round-bottomed flask was added 2-((4-fluorobenzyl)(4-(pyridin-3-yl)benzyl)amino)thiazole-5-carboxylic acid (850 mg, 2.026 mmol) in dichloromethane (10.100 ml) and the solution was cooled to 0° C. Oxalyl chloride (0.266 ml, 3.04 mmol) and dimethylformamide (0.016 ml, 0.203 mmol) were added and some bubbling occurred. The solution was warmed to room temperature and stirred for 1 hour. The mixture was cooled to 0° C., and trimethylsilyl azide (0.538 ml, 4.05 mmol) was added. The mixture was warmed to room temperature, stirred for 30 minutes and concentrated under vacuum. Toluene (5 ml) was added and the mixture was heated to 95° C. for 2.5 hours. The toluene was removed and the resulting solid was triturated/sonicated with ether and filtered with ether washes to provide the title compound.

후처리

  1. temperatureThe solution was warmed to room temperature
  2. temperatureThe mixture was cooled to 0° C.
  3. temperatureThe mixture was warmed to room temperature
  4. stirringstirred for 30 minutes
  5. concentrationconcentrated under vacuum
  6. additionToluene (5 ml) was added
  7. temperaturethe mixture was heated to 95° C. for 2.5 hours
  8. customThe toluene was removed
  9. customthe resulting solid was triturated/sonicated with ether
  10. filtrationfiltered with ether

출처 및 근거

ORD 기록
ord-e981703853f44ba6ae5c378eb5bb28c2
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302989B2

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