Acetic Acid → HCID 86682449, compound

HRID 715874Notes

Reaction equation

HRID 715874 reaction equation
[F:1][C:2]1([F:47])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30](C=O)=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[C:9]=2[CH:35]([F:46])[C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=2)[CH2:4][CH2:3]1.[C:48]([OH:51])(=O)[CH3:49].[CH3:52][NH:53][CH2:54]CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[F:1][C:2]1([F:47])[CH2:3][CH2:4][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30]([CH2:52][N:53]([CH2:49][CH2:48][OH:51])[CH3:54])=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[C:9]=2[CH:35]([F:46])[C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:43])[F:44])=[CH:38][CH:37]=2)[CH2:6][CH2:7]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 80162-(Methylamino)ethanolHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86682450HCID 86682450, compound

Product 1

HCID 86682449HCID 86682449, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 70 mg (0.11 mmol) of 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-formyl pyrimidin-2-yl)piperidin-4-yl]-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol obtained in Example (36-1) in 1.0 ml of tetrahydrofuran, 6.1 μl (0.11 mmol) of acetic acid, 26 μl (0.32 mmol) of 2-(methylamino)ethanol and 68 mg (0.32 mmol) of sodium triacetoxyborohydride were added, and the reaction solution was stirred at room temperature for 3 hours. After completion of the reaction, saturated sodium hydrogencarbonate aqueous solution was added to the reaction solution and the reaction solution was extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [dichloromethane/methanol/28% ammonia aqueous solution=95/4.75/0.25-80/19/1 (V/V/V)] to provide 68 mg of the title compound as a white solid (yield: 89%).

Workup

  1. additionwas added to the reaction solution
  2. extractionthe reaction solution was extracted with dichloromethane
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fbb991cb11e24532905683d86dfbd679
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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