[6-(Methylsulfinyl)-4-pyrimidinyl]acetonitrile → [6-({[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}amino)-4-pyrimidinyl]acetonitrile

HRID 2401223노트

반응식

HRID 2401223 반응식
CS([C:4]1[N:9]=[CH:8][N:7]=[C:6]([CH2:10][C:11]#[N:12])[CH:5]=1)=O.[F:13][C:14]([F:27])([F:26])[C:15]1[NH:25][C:18]2=[N:19][CH:20]=[C:21]([CH2:23][NH2:24])[CH:22]=[C:17]2[CH:16]=1>C(O)(C)C.C(#N)C.CS(C)=O>[F:27][C:14]([F:13])([F:26])[C:15]1[NH:25][C:18]2=[N:19][CH:20]=[C:21]([CH2:23][NH:24][C:4]3[N:9]=[CH:8][N:7]=[C:6]([CH2:10][C:11]#[N:12])[CH:5]=3)[CH:22]=[C:17]2[CH:16]=1

참가 물질

6

반응물 2

HCID 67111377[6-(Methylsulfinyl)-4-pyrimidinyl]acetonitrile2회HCID 671114591H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)-2회

생성물 1

HCID 51355873[6-({[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}amino)-4-pyrimidinyl]acetonitrile수율 8.4%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 3776Isopropanol용매HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

A mixture of [6-(methylsulfinyl)-4-pyrimidinyl]acetonitrile (Intermediate 16, 150 mg, 0.828 mmol) and 1-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 178 mg, 0.828 mmol) in isopropanol (7 mL) was stirred and heated at 80° C. overnight. The reaction mixture was cooled to room temperature and condensed. This solid was dissolved in a mixture of acetonitrile and DMSO (1:1) (2.7 mL) and purified by MDAP (3 injections). Fractions containing the suspected product were combined and concentrated under reduced pressure. The solid was dissolved in a mixture of acetonitrile and DMSO (1:1) (1.8 mL) and purified again by MDAP (2 injections). Fractions containing the suspected product were combined and concentrated under reduced pressure to give the title compound as a solid (23 mg);

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customcondensed
  3. custompurified by MDAP (3 injections)
  4. additionFractions containing the suspected product
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe solid was dissolved in a mixture of acetonitrile and DMSO (1:1) (1.8 mL)
  7. custompurified again by MDAP (2 injections)
  8. additionFractions containing the suspected product
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9d72a881b07642888a97df947162342b
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796283B2

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