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Trimethylsilyl isocyanate → 1-(1-(5-(5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutyl)urea

HRID 2362734
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HRID 2362734 반응식
[Cl:1][C:2]1[C:3]([C:27]2[S:31][C:30]([C:32]3([NH2:36])[CH2:35][CH2:34][CH2:33]3)=[N:29][CH:28]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[N:8]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:5]2=[N:6][CH:7]=1.C[Si]([N:41]=[C:42]=[O:43])(C)C>O1CCCC1.O>[Cl:1][C:2]1[C:3]([C:27]2[S:31][C:30]([C:32]3([NH:36][C:42]([NH2:41])=[O:43])[CH2:33][CH2:34][CH2:35]3)=[N:29][CH:28]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[N:8]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:5]2=[N:6][CH:7]=1
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참가 물질

5

반응물 2

HCID 70696Trimethylsilyl isocyanate2회HCID 670037141-(5-(5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanamine

생성물 1

HCID 670034511-(1-(5-(5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutyl)urea

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

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온도
70 °C

실험 절차

A mixture of 1-(5-(5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanamine (40 mg, 0.074 mmol) (Example 121A) in anhydrous tetrahydrofuran (1 mL) was treated with trimethylsilyl isocyanate (0.049 ml, 0.371 mmol), and the reaction mixture was heated to 70° C. for 5 hours. Additional trimethylsilyl isocyanate (0.025 ml, 0.185 mmol) was added, and the reaction solution was heated for 16 hours at 70° C. The reaction was cooled, diluted with water, and extracted with dichloromethane. The organic extracts were combined and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with 5% methanol in dichloromethane, to provide the title compound. MS ESI(+) m/z 582.3 [M+H]+.

후처리

  1. temperaturethe reaction solution was heated for 16 hours at 70° C
  2. temperatureThe reaction was cooled
  3. extractionextracted with dichloromethane
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting with 5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-6bf54e86d8d341a39eb167b633b88812
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691810B2

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