Phenylglyoxylic Acid → HCID 59828535, compound

HRID 220331Notes

Reaction equation

HRID 220331 reaction equation
[C:1]([C:9]([OH:11])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][N:13]([CH3:20])[CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.CCN(C(C)C)C(C)C.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH3:12][N:13]([CH3:20])[CH:14]1[CH2:19][CH2:18][N:17]([C:9](=[O:11])[C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:8])[CH2:16][CH2:15]1

Participants

7

Reactant 5

HCID 11915Phenylglyoxylic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 417391N,N-Dimethylpiperidin-4-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 59828535HCID 59828535, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoylformic acid (1.0 g, 6.7 mmol), dimethylpiperidin-4-ylamine (854 mg, 6.7 mmol), DIPEA (3.5 mL, 20.0 mmol), and 1-hydroxybenzotriazole (1.4 g, 10 mmol) were dissolved in 20 mL of methylene chloride, then N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.53 g, 7.99 mmol) was added and the mixture was stirred at room temperature for 16 hours. The mixture was extracted with a 1.0 N NaOH solution, then the organic layer was dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (10-30% MeOH in methylene chloride gradient) to give intermediate (5a) (501 mg).

Workup

  1. extractionThe mixture was extracted with a 1.0 N NaOH solution
  2. dry with materialthe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (10-30% MeOH in methylene chloride gradient)

Sources & evidence

ORD record
ord-edce996584d54db9ad734106d3dfb205
Source dataset
uspto-grants-2012_06
Patent number
US08202891B2

Reaction notes

Loading…