Piperidine → 2-[(5-chloro-1H-indol-3-yl)methyl]-7-isobutyl-5-methyl-3-(3-methylisoxazol-4yl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 1181844Notes

Reaction equation

HRID 1181844 reaction equation
[CH2:1]([N:5]1[C:10]([NH:11][N:12]=[CH:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([Cl:23])[CH:21]=3)[NH:16][CH:15]=2)=[CH:9][C:8](=[O:24])[N:7]([CH3:25])[C:6]1=[O:26])[CH:2]([CH3:4])[CH3:3].[O:27]1[CH:31]=[CH:30][C:29]([CH:32]=O)=[N:28]1.N1CCCC[CH2:35]1.O1C=CC=N1>CN(C)C=O.O.C(OCC)(=O)C>[Cl:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:13][N:12]1[C:35]([C:30]2[C:29]([CH3:32])=[N:28][O:27][CH:31]=2)=[C:9]2[C:10]([N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:6](=[O:26])[N:7]([CH3:25])[C:8]2=[O:24])=[N:11]1

Participants

8

Reactant 4

HCID 8082PiperidineHCID 9254IsoxazoleHCID 183730781,2-Oxazole-3-carbaldehydeHCID 1363341125-chloro-1H-indole-3-carbaldehyde (3-isobutyl-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazone

Product 1

HCID 589810552-[(5-chloro-1H-indol-3-yl)methyl]-7-isobutyl-5-methyl-3-(3-methylisoxazol-4yl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Chloro-1H-indole-3-carbaldehyde(3-isobutyl-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazone (100 mg) was added to a solution of isoxazolaldehyde (86 mg) in dimethylformamide at RT. Piperidine (100 uL) was then added and brought to 80 C for 8 h. After cooling to RT, ethyl acetate (25 mL) was added to brown solution and water (25 mL) was added and extracted. The aqueous layer was back extract with ethyl acetate and then combined. The organic layer was dried over sodium sulfate, filtered and removal of solvent to give an amorphous solid. The isoxazole was submitted the Gilson Preparatory chromatography to give a 100 mg of white solids. ES M+H+467.

Workup

  1. additionwas added
  2. extractionextracted
  3. extractionThe aqueous layer was back extract with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customremoval of solvent
  7. customto give an amorphous solid

Sources & evidence

ORD record
ord-e70ab77086a047909137d39918ee7684
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

Loading…