Morpholine → HCID 23122062, compound

HRID 1713536Notes

Reaction equation

HRID 1713536 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([NH:13][CH2:14][C:15](O)=[O:16])=[O:12])[CH2:10][CH:5]2[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:3]1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[N:30]1([C:15](=[O:16])[CH2:14][NH:13][C:11]([N:9]2[CH2:8][CH2:7][N:6]3[C:2](=[O:1])[O:3][C:4]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:5]3[CH2:10]2)=[O:12])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23122089HCID 23122089, compound

Product 1

HCID 23122062HCID 23122062, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[(Tetrahydro-3-oxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-7(1H)-yl)carbonyl]glycine (0.15 g, 0.38 mmol) was dissolved in N,N-dimethylformamide (3 mL). Morpholine (0.14 g, 1.2 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.15 g, 0.76 mmol) and 1-hydroxybenzotriazole (0.11 g, 0.77 mmol) were added thereto, and the mixture was stirred at room temperature for 20 hours. To the reaction solution was added ice water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, an aqueous saturated sodium hydrogen carbonate solution and water and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:methanol=95:5) and powder was formed from hexane to obtain the title compound (90 mg, yield 51%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. concentrationan aqueous saturated sodium hydrogen carbonate solution and water and then concentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (ethyl acetate:methanol=95:5)
  5. custompowder was formed from hexane

Sources & evidence

ORD record
ord-7d031e4d0edc4da0bf25cc5bfcb2563f
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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