Methyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-cyano-2-(4-fluoro-3-methylphenylamino)nicotinate → tert-Butyl (1S,2R)-2-(4-(4-fluoro-3-methylphenylamino)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

HRID 711453노트

반응식

HRID 711453 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[CH:25]=[C:24]([C:26]#[N:27])[C:19]([C:20]([O:22]C)=O)=[C:18]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[C:31]([CH3:36])[CH:30]=2)[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.CC(O)=O.[Pt]=O>[F:35][C:32]1[CH:33]=[CH:34][C:29]([NH:28][C:18]2[C:19]3[C:20](=[O:22])[NH:27][CH2:26][C:24]=3[CH:25]=[C:16]([NH:15][C@@H:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:9]3[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[N:17]=2)=[CH:30][C:31]=1[CH3:36]

참가 물질

5

반응물 1

HCID 67237937Methyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-cyano-2-(4-fluoro-3-methylphenylamino)nicotinate

생성물 1

HCID 86654707tert-Butyl (1S,2R)-2-(4-(4-fluoro-3-methylphenylamino)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate수율 70.6%

시약·촉매·용매 3

HCID 82844Platinum oxide (PtO)촉매HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

A mixture of methyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-cyano-2-(4-fluoro-3-methylphenylamino)nicotinate (75 mg, 0.151 mmol) and platinum oxide (34.2 mg, 0.151 mmol) in DCM (2 mL) and HOAc (0.5 mL) was stirred at RT under H2 atmosphere. The mixture was subsequently filtered through Celite. The filtrate was concentrated and the residue was purified by preparative HPLC to give the title compound (50 mg, 70.6%). [M+H] calc'd for C25H32FN5O3, 470. found, 470.

후처리

  1. filtrationThe mixture was subsequently filtered through Celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-8a024c68f77e492d88a8776f7203211b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181255B2

반응 노트

불러오는 중…