Potassium Carbonate → HCID 59415882, compound

HRID 2061838Notes

Reaction equation

HRID 2061838 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 59415882HCID 59415882, compoundYield 17.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

(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%).

Workup

  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)

Sources & evidence

ORD record
ord-c8240f9521c3433995b57668200d5f3a
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

Loading…