Potassium Carbonate → HCID 59415882, 화합물

HRID 2061838노트

반응식

HRID 2061838 반응식
[CH2:1]([NH:3][C:4](=[O:43])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([C@@H:22]2[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]2)[CH:17]=[C:16]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:15]3=[O:33])=[C:8]([C:34]2[S:35][CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[N:38]=2)[CH:7]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:52][CH2:53][N:54]([CH2:57][CH3:58])[CH2:55][CH3:56]>CN(C=O)C.CCOC(C)=O>[CH2:53]([N:54]([CH2:57][CH3:58])[CH2:55][CH2:56][N:24]1[CH2:25][CH2:26][CH2:27][C@@H:22]([N:18]2[C:19]3[C:14](=[CH:13][C:12]([C:9]4[CH:10]=[N:11][C:6]([NH:5][C:4]([NH:3][CH2:1][CH3:2])=[O:43])=[CH:7][C:8]=4[C:34]4[S:35][CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[N:38]=4)=[CH:21][CH:20]=3)[C:15](=[O:33])[C:16]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:17]2)[CH2:23]1)[CH3:52]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 59415752HCID 59415752, 화합물

생성물 1

HCID 59415882HCID 59415882, 화합물수율 17.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

(R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1-(piperidin-3-yl)-1,4-dihydroquinoline-3-carboxylate (Example 262, 0.100 g, 0.16 mmol) was taken up in DMF (2 mL), K2CO3 (0.112 g, 0.81 mmol) and 2-chloro-N,N-diethylethanamine hydrochloride (0.031 g, 0.18 mmol) were added. The mixture was heated to 100° C. overnight then the reaction was cooled to room temperature and diluted with EtOAc. The organic layer was washed with brine twice and water twice, then the solvent was removed in vacuo and the residue was purified by flash column chromatography on silica gel using (dichloromethane-methanol) to give (R)-ethyl 1-(1-(2-(diethylamino)ethyl)piperidin-3-yl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.020 g, 17%).

후처리

  1. temperaturethe reaction was cooled to room temperature
  2. washThe organic layer was washed with brine twice
  3. customwater twice, then the solvent was removed in vacuo
  4. customthe residue was purified by flash column chromatography on silica gel using (dichloromethane-methanol)

출처 및 근거

ORD 기록
ord-c8240f9521c3433995b57668200d5f3a
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283361B2

반응 노트

불러오는 중…