Potassium Carbonate → HCID 59415882、化合物

HRID 2061838ノート

反応式

HRID 2061838 の反応式
[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]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 59415752HCID 59415752、化合物

生成物 1

HCID 59415882HCID 59415882、化合物収率 17.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

(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%).

後処理

  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)

出典と根拠

ORDレコード
ord-c8240f9521c3433995b57668200d5f3a
出典データセット
uspto-grants-2012_10
特許番号
US08283361B2

反応ノート

読み込み中…