Hydrochloric Acid → HCID 66703740, compound

HRID 426010Notes

Reaction equation

HRID 426010 reaction equation
Cl.C([O:9][C@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[NH:16][C:17]1[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][C:18]=1[C:19]([NH:21][C:22]1[CH:31]=[C:30]2[C:25]([CH2:26][CH2:27][C:28](=[O:33])[N:29]2[CH3:32])=[CH:24][CH:23]=1)=[O:20])C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>[C].[Pd].C(O)C>[OH:9][C@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[NH:16][C:17]1[CH:37]=[C:36]([C:38]([F:41])([F:39])[F:40])[CH:35]=[CH:34][C:18]=1[C:19]([NH:21][C:22]1[CH:31]=[C:30]2[C:25]([CH2:26][CH2:27][C:28](=[O:33])[N:29]2[CH3:32])=[CH:24][CH:23]=1)=[O:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 66703774HCID 66703774, compound

Product 1

HCID 66703740HCID 66703740, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

At room temperature, 1 M hydrochloric acid (0.38 mL) was added to an ethanol (20 mL) solution of 2-{[(1S,2S)-2-(benzyloxy)cyclohexyl]amino}-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-4-(trifluoromethyl)benzamide (140 mg), 10% palladium-carbon (240 mg) was added, followed by stirring for 1 day under an atmosphere of hydrogen. After neutralizing with a saturated sodium bicarbonate aqueous solution extracting with chloroform, the organic layer was concentrated under a reduced pressure. By purifying the residue by silica gel column chromatography (hexane:ethyl acetate, 1:0 to 1:1), 2-{[(1S,2S)-2-hydroxycyclohexyl]amino}-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-4-(trifluoromethyl)benzamide (66 mg) was obtained as an amorphous.

Workup

  1. additionwas added
  2. extractionextracting with chloroform
  3. concentrationthe organic layer was concentrated under a reduced pressure
  4. customBy purifying the residue by silica gel column chromatography (hexane:ethyl acetate, 1:0 to 1:1)

Sources & evidence

ORD record
ord-3f9d93f54ccd4c6f81cedf37b3710807
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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