1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-N-(6-Fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide
반응식
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@:9]1([CH3:16])[C:13]([OH:15])=O)=O)(C)(C)C.[F:17][C:18]1[N:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[F:17][C:18]1[N:23]=[CH:22][C:21]([NH:24][C:13]([C@:9]2([CH3:16])[CH2:10][CH2:11][CH2:12][NH:8]2)=[O:15])=[CH:20][CH:19]=1참가 물질
반응물 5
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- 65 °C
실험 절차
To a stirred solution of (5)-1-(tert-butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid (1.0 g, 4.37 mmol) and 6-fluoropyridin-3-amine (1.47 g, 13.1 mmol), 1-hydroxybenzotriazole (0.65 mg, 4.81 mmol), and N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide (2.5 g, 13.1 mmol) in N-methylpyrrolidinone (10 mL) was added diisopropylethylamine (3.8 mL, 21.8 mmol). The reaction mixture was heated to 65° C. for 12 h and the solvent was evaporated to dryness. The residue was separated by preparative HPLC. The crude product was dissolved in methanol and 4N HCl in dioxane (4 mL) was added. The reaction mixture was stirred at room temperature overnight and the crude product was used in the next step without further purification. LC/MS [M+H]+: 224; Ret time (Method F): 0.78 min.
후처리
- customthe solvent was evaporated to dryness
- customThe residue was separated by preparative HPLC
- dissolutionThe crude product was dissolved in methanol
- addition4N HCl in dioxane (4 mL) was added
- customthe crude product was used in the next step without further purification
- custom0.78 min.
출처 및 근거
- ORD 기록
- ord-0e5787db47444ff19c26f8631e4f81a0
- 출처 데이터셋
- uspto-grants-2013_04
- 특허 번호
- US08415340B2
반응 노트
불러오는 중…