반응식
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8](=O)OC(C)(C)C.[Cl:15]C1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=1.CCN(C(C)C)C(C)C.Cl.O1CCOCC1>CO.CS(C)=O>[ClH:15].[F:23][C:22]([F:25])([F:24])[C:19]1[CH:20]=[CH:21][C:8]([NH:7][C@H:3]2[CH2:4][CH2:5][CH2:6][C@@H:2]2[NH2:1])=[N:17][CH:18]=1참가 물질
반응 조건
- 온도
- 140 °C
실험 절차
A microwave vial was charged with tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 1.0 g, 4.99 mmol), 2-chloro-5-(trifluoromethyl)pyridine (CAS number 52334-81-3; 0.997 g, 5.49 mmol), DIPEA (2.62 ml, 14.98 mmol) and DMSO (16.6 ml). The reaction was heated with microwave irradiation at 140° C. for 2 hours and then partitioned between ethyl acetate and water. The organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. This was then purified by column chromatography (silica, 0-50% ethyl acetate/petrol) to afford a cream solid to which was then added methanol (10 ml) and HCl in 1,4-dioxane (4M, 6.24 ml, 24.97 mmol) and the reaction was stirred at room temperature for 17 hours. The reaction mixture was concentrated in vacuo and azeotropically distilled with toluene to afford the title compound.
후처리
- custompartitioned between ethyl acetate and water
- washThe organics were washed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThis was then purified by column chromatography (silica, 0-50% ethyl acetate/petrol)
- customto afford a cream solid to which
- concentrationThe reaction mixture was concentrated in vacuo
- distillationazeotropically distilled with toluene
출처 및 근거
- ORD 기록
- ord-adfe6d8e595d40458419aeedf13db212
- 출처 데이터셋
- uspto-grants-2015_10
- 특허 번호
- US09156829B2
연결된 노트
불러오는 중…