Hydrochloric Acid → HCID 66703635, compound

HRID 426015Notes

Reaction equation

HRID 426015 reaction equation
Cl.[Si]([O:9][CH2:10][CH2:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([NH:22][C:23](=[O:41])[C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:25]=3[NH:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[CH:20]=2)[CH2:15][CH2:14][C:13]1=[O:42])(C(C)(C)C)(C)C>C(O)C>[CH:35]1([NH:34][C:25]2[CH:26]=[C:27]([C:30]([F:33])([F:31])[F:32])[CH:28]=[CH:29][C:24]=2[C:23]([NH:22][C:19]2[CH:20]=[C:21]3[C:16]([CH2:15][CH2:14][C:13](=[O:42])[N:12]3[CH2:11][CH2:10][OH:9])=[CH:17][CH:18]=2)=[O:41])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66703584HCID 66703584, compound

Product 1

HCID 66703635HCID 66703635, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 M Hydrochloric acid (0.37 mL) was added to an ethanol solution (1.5 mL) of N-[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl]-2-(cyclohexylamino)-4-(trifluoromethyl)benzamide (220 mg), followed by stirring at room temperature for 5 hours. The reaction liquid was concentrated under a reduced pressure, and a sodium bicarbonate aqueous solution was added to the residue, followed by extraction with ethyl acetate. After drying the organic layer with sodium sulfate, the solution was concentrated under a reduced pressure. By purifying the residue by silica gel column chromatography (hexane:ethyl acetate, 2:1 to 2:3), 2-(cyclohexylamino)-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl]-4-(trifluoromethyl)benzamide (148 mg) was obtained as a solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under a reduced pressure
  3. additiona sodium bicarbonate aqueous solution was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialAfter drying the organic layer with sodium sulfate
  6. concentrationthe solution was concentrated under a reduced pressure
  7. customBy purifying the residue by silica gel column chromatography (hexane:ethyl acetate, 2:1 to 2:3)

Sources & evidence

ORD record
ord-9ba6e86baa7944e28175353b01fa4e43
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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