Diethylamine → HCID 10203588, compound

HRID 229668Notes

Reaction equation

HRID 229668 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:28])[N:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:12]=[C:13]([C:15]2[CH:19]=[CH:18][S:17][C:16]=2[CH:20]=O)[CH:14]=1)#[N:2].[CH2:29]([NH:31][CH2:32][CH3:33])[CH3:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O1CCCC1.C(O)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:28])[N:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:12]=[C:13]([C:15]2[CH:19]=[CH:18][S:17][C:16]=2[CH2:20][N:31]([CH2:32][CH3:33])[CH2:29][CH3:30])[CH:14]=1)#[N:2]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 10293257HCID 10293257, compound

Product 1

HCID 10203588HCID 10203588, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 20 mg of 3-(2-cyanophenyl)-5-(2-formylthiophen-3-yl)-1-phenyl-1,2-dihydropyridin-2-one, 0.1 ml of a 2M solution of diethylamine in tetrahydrofuran and 0.1 ml acetic acid in 2 ml of tetrahydrofuran was stirred at room temperature for 15 minutes, 20 mg of sodium triacetoxyborohydride were added and the mixture was stirred for 3 hours more. A 2N aqueous solution of sodium hydroxide was added thereto, the mixture was extracted with ethyl acetate and the organic layer was washed with water and a saturated saline solution and dried over magnesium sulfate. The solvent was concentrated in vacuo and the residue was purified by an NH silica gel column chromatography to give 15 mg of the title compound as white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. dry with materiala saturated saline solution and dried over magnesium sulfate
  4. concentrationThe solvent was concentrated in vacuo
  5. customthe residue was purified by an NH silica gel column chromatography

Sources & evidence

ORD record
ord-edcfc907a9fd4447bedc35ecf59578d7
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

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