Trifluoroacetic acid → 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methanesulfonyl-pyrrolidin-3-yl)-amide

HRID 2191569노트

반응식

HRID 2191569 반응식
[CH3:1][S:2]([N:5]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([CH:22]4[CH2:24][CH2:23]4)[N:20]=3)[N:15](COCC[Si](C)(C)C)[CH:14]=2)=[O:12])[CH2:6]1)(=[O:4])=[O:3].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][S:2]([N:5]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([CH:22]4[CH2:24][CH2:23]4)[N:20]=3)[NH:15][CH:14]=2)=[O:12])[CH2:6]1)(=[O:4])=[O:3]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 670022002-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methanesulfonyl-pyrrolidin-3-yl)-amide

생성물 1

HCID 547557402-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methanesulfonyl-pyrrolidin-3-yl)-amide수율 43.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a 10 mL round-bottomed flask, 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methanesulfonyl-pyrrolidin-3-yl)-amide (177 mg, 0.37 mmol) was dissolved in CH2Cl2 (3 mL). Trifluoroacetic acid (1.1 mL) was added and the light yellow reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was taken up in toluene (5 mL), concentrated and then dried under high vacuum. The residue was dissolved in CH2Cl2 (2.5 mL) and ethylenediamine (1.5 mL) was added. The reaction mixture was stirred at room temperature overnight then diluted with MeOH and the solid precipitate was collected via filtration. The solid residue was rinsed with hot water and EtOAc then dried under high vacuum to afford 56 mg (43%) of 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methanesulfonyl-pyrrolidin-3-yl)-amide as a white solid. MS: (M+H)+=350; mp>300.

후처리

  1. concentrationthen concentrated
  2. concentrationconcentrated
  3. customdried under high vacuum
  4. dissolutionThe residue was dissolved in CH2Cl2 (2.5 mL)
  5. additionethylenediamine (1.5 mL) was added
  6. stirringThe reaction mixture was stirred at room temperature overnight
  7. additionthen diluted with MeOH
  8. filtrationthe solid precipitate was collected via filtration
  9. washThe solid residue was rinsed with hot water and EtOAc
  10. customthen dried under high vacuum

출처 및 근거

ORD 기록
ord-0bcb45b38cb547a3a7b03cf892a90b4e
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329699B2

반응 노트

불러오는 중…