Sodium Bicarbonate → HCID 76372266, compound

HRID 715850Notes

Reaction equation

HRID 715850 reaction equation
[F:1][C:2]1([F:65])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[CH:16]([O:18]CC4C=CC(OC)=CC=4)[CH2:15][C:14]([CH3:29])([CH3:28])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:35][CH2:34][N:33]([C:36]4[N:41]=[CH:40][C:39]([N:42]5[CH2:47][CH2:46][CH:45]([C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:44][CH2:43]5)=[CH:38][N:37]=4)[CH2:32][CH2:31]3)[C:9]=2[CH:53]([F:64])[C:54]2[CH:59]=[CH:58][C:57]([C:60]([F:63])([F:62])[F:61])=[CH:56][CH:55]=2)[CH2:4][CH2:3]1.Cl.O1CCOCC1.C(=O)([O-])O.[Na+]>C(O)C>[F:65][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:28])([CH3:29])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:35][CH2:34][N:33]([C:36]4[N:37]=[CH:38][C:39]([N:42]5[CH2:47][CH2:46][CH:45]([C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:44][CH2:43]5)=[CH:40][N:41]=4)[CH2:32][CH2:31]3)[C:9]=2[CH:53]([F:64])[C:54]2[CH:55]=[CH:56][C:57]([C:60]([F:63])([F:62])[F:61])=[CH:58][CH:59]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 86682428HCID 86682428, compound

Product 1

HCID 76372266HCID 76372266, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 98 mg (0.11 mmol) of 4-(4,4-Difluorocyclohexyl)-2-(1-{5-[4-(ethoxycarbonyl)piperidin-1-yl]pyrimidin-2-yl}piperidin-4-yl)-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 13, in 2 ml of ethanol, 1 ml of 4 N hydrogen chloride/1,4-dioxane solution was added, and the reaction solution was stirred at 50° C. for 3 hours. After completion of the reaction, saturated sodium hydrogencarbonate aqueous solution was poured into the reaction solution under ice cooling and the reaction solution was 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=90/10-60/40 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure to provide 69 mg of the title compound as a light brown solid (yield: 81%).

Workup

  1. additionwas poured into the reaction solution under ice cooling
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride aqueous solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-29470a2456ab427ba78f8fedd09408d8
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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