Hydrochloric Acid → HCID 76372416, compound

HRID 715859Notes

Reaction equation

HRID 715859 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][C:10]([N:13]3[CH2:18][CH2:17][CH:16]([C:19]4[C:28]([CH:29]([F:40])[C:30]5[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=5)=[C:27]([CH:41]5[CH2:46][CH2:45][C:44]([F:48])([F:47])[CH2:43][CH2:42]5)[C:26]5[CH:25]([O:49]CC6C=CC(OC)=CC=6)[CH2:24][C:23]([CH3:60])([CH3:59])[CH2:22][C:21]=5[N:20]=4)[CH2:15][CH2:14]3)=[N:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.Cl.C(=O)([O-])O.[Na+]>O1CCOCC1>[C:1]1([C:7]2[CH:12]=[N:11][C:10]([N:13]3[CH2:18][CH2:17][CH:16]([C:19]4[C:28]([CH:29]([F:40])[C:30]5[CH:35]=[CH:34][C:33]([C:36]([F:37])([F:38])[F:39])=[CH:32][CH:31]=5)=[C:27]([CH:41]5[CH2:46][CH2:45][C:44]([F:47])([F:48])[CH2:43][CH2:42]5)[C:26]5[CH:25]([OH:49])[CH2:24][C:23]([CH3:60])([CH3:59])[CH2:22][C:21]=5[N:20]=4)[CH2:15][CH2:14]3)=[N:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86682430HCID 86682430, compound

Product 1

HCID 76372416HCID 76372416, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To 78 mg (0.094 mmol) of 2-{1-[5-(Cyclohex-1-en-1-yl)pyrimidin-2-yl]piperidin-4-yl}-4-(4,4-difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinoline, which was prepared by a method similar to that of Reference Example 18, 0.4 ml of 6 N hydrochloric acid and 2 ml of 1,4-dioxane were added, and the reaction solution was stirred at 80° C. for 3 hours. After completion of the reaction, the reaction solution was poured into saturated sodium hydrogencarbonate aqueous solution and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=95/5-80/20 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure. Diethyl ether was added to the obtained residue and the precipitate was obtained by filtration to provide 45 mg of the title compound as a white solid (yield: 67%).

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride aqueous solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. concentrationwas concentrated under reduced pressure
  8. additionDiethyl ether was added to the obtained residue
  9. customthe precipitate was obtained by filtration

Sources & evidence

ORD record
ord-5cb5a5b764c44d8eb17c88d06ebc83df
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

Loading…