1-Hydroxybenzotriazole → HCID 23121826, compound

HRID 1713557Notes

Reaction equation

HRID 1713557 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:23]1[C:32]2[C:27](=[CH:28][C:29]([C:33](O)=[O:34])=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[C:17]1([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:11]3[CH2:12][N:13]([C:33]([C:29]4[CH:28]=[C:27]5[C:32](=[CH:31][CH:30]=4)[N:23]=[CH:24][CH:25]=[CH:26]5)=[O:34])[CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 825716-Quinolinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23121826HCID 23121826, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.15 g, 0.51 mmol), quinoline-6-carboxylic acid (0.11 g, 0.63 mmol), 1-hydroxybenzotriazole (0.10 g, 0.74 mmol) were dissolved in N,N-dimethylformamide (5 mL). 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.15 g, 0.78 mmol) was added thereto, and the mixture was stirred at room temperature for 2 hours and 30 minutes. The reaction solution was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with a 1 N aqueous sodium hydroxide solution, water and saturated brine, and dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated. The residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate) and concentrated. The residue was recrystallized from ethyl acetate-hexane to obtain the title compound (0.13 g, yield 57%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a 1 N aqueous sodium hydroxide solution, water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe solid was filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3c95dd6c7f8b4190ab8f1acff548c9b6
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

Loading…