Dimethylformamide → HCID 10025434, compound

HRID 1794274Notes

Reaction equation

HRID 1794274 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[N:17]2[CH2:18][C:19]3[C:24]([C:16]2=[N:15][N:14]=1)=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3.C(=O)([O-])[O-].[K+].[K+].ClC[C:34]1[CH:35]=[N:36][N:37]([CH3:39])N=1.[CH3:40][N:41](C=O)C>O>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[N:17]2[CH2:18][C:19]3[C:24]([C:16]2=[N:15][N:14]=1)=[CH:23][C:22]([O:25][CH2:34][C:35]1[N:41]=[CH:40][N:37]([CH3:39])[N:36]=1)=[CH:21][CH:20]=3

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 222209104-Chloromethyl-2-methyl-2H-[1,2,3]triazoleHCID 22220927HCID 22220927, compound

Product 1

HCID 10025434HCID 10025434, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(5-Methyl-3-phenylisoxazol-4-yl)-5H-[1,2,4]triazolo[3,4-a]isoindol-8-ol (35 mg) and potassium carbonate (30 mg) and 5-(chloromethyl)-2-methyltriazole were heated together with DMF (1 ml) at 120° C. for 2 hours. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with water (×5), dried and evaporated to yield an oil which was purified by column chromatography on silica using methanol/dichloromethane to yield the title compound (7.8 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water (×5)
  3. customdried
  4. customevaporated
  5. customto yield an oil which
  6. customwas purified by column chromatography on silica

Sources & evidence

ORD record
ord-2915b8405f504e80929c582a49a82fd7
Source dataset
uspto-grants-2006_04
Patent number
US07022724B2

Reaction notes

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