Triethylamine → HCID 57652127, 화합물
반응식
[C:1]1([C:7]2[O:8][C:9]([C:15]([F:18])([F:17])[F:16])=[C:10]([C:12]([OH:14])=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.[CH2:50]([O:52][C:53]([CH:55]1[CH2:60][CH2:59][N:58]([C:61]2[CH:66]=[CH:65][C:64]([NH2:67])=[CH:63][CH:62]=2)[CH2:57][CH2:56]1)=[O:54])[CH3:51]>CN(C=O)C>[CH2:50]([O:52][C:53]([CH:55]1[CH2:56][CH2:57][N:58]([C:61]2[CH:66]=[CH:65][C:64]([NH:67][C:12]([C:10]3[N:11]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[O:8][C:9]=3[C:15]([F:18])([F:17])[F:16])=[O:14])=[CH:63][CH:62]=2)[CH2:59][CH2:60]1)=[O:54])[CH3:51]참가 물질
실험 절차
A mixture of 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (926 mg, 3.6 mmol), triethylamine (910 mg, 1.25 mL, 9.0 mmol), bromotripyrrolidinophosphonium hexafluorophosphate (PyBroP, 2.51 g, 5.4 mmol) and 1-(4-amino-phenyl)-piperidine-4-carboxylic acid ethyl ester (3.6 mmol, prepared above) in DMF (10 mL) was stirred at room temperature overnight. The reaction mixture was diluted with. EtOAc, and washed twice with water. The organic phase was then dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel (gradient elution with 10-50% ethyl acetate in hexanes) to provide 1-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid ethyl ester. HRMS calcd for C25H24F3N3O4 (M+H) 488.1792, obsd 488.1792.
후처리
- additionThe reaction mixture was diluted with
- washEtOAc, and washed twice with water
- dry with materialThe organic phase was then dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by chromatography on silica gel (gradient elution with 10-50% ethyl acetate in hexanes)
출처 및 근거
- ORD 기록
- ord-235c9035034442fe9de86c4c3d04f808
- 출처 데이터셋
- uspto-grants-2012_07
- 특허 번호
- US08211914B2
반응 노트
불러오는 중…