Isothiocyanatotrimethylsilane → Pf-06282999

HRID 77531

반응식

HRID 77531 반응식
[NH2:1][C:2](=[O:21])[CH2:3][NH:4]/[C:5](/[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])=[CH:6]\[C:7]([O:9]CC)=O.C[Si]([N:26]=[C:27]=[S:28])(C)C>C(OCCCC)(=O)C.CN(C=O)C>[Cl:18][C:16]1[CH:15]=[CH:14][C:13]([O:19][CH3:20])=[C:12]([C:5]2[N:4]([CH2:3][C:2]([NH2:1])=[O:21])[C:27](=[S:28])[NH:26][C:7](=[O:9])[CH:6]=2)[CH:17]=1

참가 물질

5

반응물 2

HCID 75297IsothiocyanatotrimethylsilaneHCID 86684671(Z)-Ethyl 3-((2-amino-2-oxoethyl)amino)-3-(5-chloro-2-methoxyphenyl)acrylate

생성물 1

HCID 71571306Pf-06282999

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 31272Butyl Acetate용매2회

반응 조건

온도
117.5 °C

실험 절차

A slurry of (Z)-ethyl 3-((2-amino-2-oxoethyl)amino)-3-(5-chloro-2-methoxyphenyl)acrylate (20 g, 63 mmol) in a mixture of butyl acetate (140 mL) and DMF (38 mL) was treated with trimethylsilyl isothiocyanate (16.8 g, 125 mmol) and the mixture was heated at 115-120° C. for 5-6 hours. The mixture was cooled to 0-5° C., butyl acetate (100 mL) was added and the mixture was slurried for 8 hours. The formed solids were filtered, and the filter cake was washed with butyl acetate (2×100 mL). The solid was dried in a vacuum oven at 50° C. for 12 hours to a tan solid. The solid was dissolved in a 5:1 mixture of DMF and water at room temperature and additional water was added slowly to crystallize the material. The slurry was cooled to 10° C. and stirred for 8 hours, followed by filtration and washing with water. The filter cake was dried in a vacuum oven at 50° C. for 8 hours. The solid was dissolved in a 1:1 mixture of methanol and water and the slurry was heated to 50° C. and held at this temperature for 2 hours. After cooling to 10° C. over 30 minutes, the slurry was held at this temperature for 1 hour, filtered and washed with water and dried in a vacuum oven at 50° C. for 8 hours to give the title compound as a white solid.

후처리

  1. temperatureThe mixture was cooled to 0-5° C.
  2. filtrationThe formed solids were filtered
  3. washthe filter cake was washed with butyl acetate (2×100 mL)
  4. customThe solid was dried in a vacuum oven at 50° C. for 12 hours to a tan solid
  5. dissolutionThe solid was dissolved in a 5:1 mixture of DMF and water at room temperature
  6. additionadditional water was added slowly
  7. customto crystallize the material
  8. temperatureThe slurry was cooled to 10° C.
  9. filtrationfollowed by filtration
  10. washwashing with water
  11. customThe filter cake was dried in a vacuum oven at 50° C. for 8 hours
  12. dissolutionThe solid was dissolved in a 1:1 mixture of methanol and water
  13. temperaturethe slurry was heated to 50° C.
  14. waitheld at this temperature for 2 hours
  15. temperatureAfter cooling to 10° C. over 30 minutes
  16. waitthe slurry was held at this temperature for 1 hour
  17. filtrationfiltered
  18. washwashed with water
  19. customdried in a vacuum oven at 50° C. for 8 hours

출처 및 근거

ORD 기록
ord-ebd56dd01ffb47d792ef2f6beb0c3f33
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841314B2

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