HCID 178469519, compound → HCID 178489579, compound

HRID 402722Notes

Reaction equation

HRID 402722 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])=[C:13](C(OCC)=O)[C:12]2=[O:30])=[CH:2]1>CN(C)C=O.CC(O)CC>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[C:12](=[O:30])[CH:13]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])[O:15]2)=[CH:2]1

Participants

4

Reactant 1

HCID 178469519HCID 178469519, compound

Product 1

HCID 178489579HCID 178489579, compoundYield 12.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6568(+-)-2-ButanolSolvent

Procedure

A solution of the compound (0.099 g, 0.24 mmol) of Example 7 in N,N-dimethylformamide (2.0 mL) was refluxed for 9 h. Cooled to ambient temperature, the reaction mixture was diluted with 2-butanol and washed with 4M sodium hydroxide solution. The organic layer was concentrated then purified by chromatography on silica gel(chloroform/methanol) to afford the titled compound as solid (0.0097 g, y. 12%).

Workup

  1. washwashed with 4M sodium hydroxide solution
  2. concentrationThe organic layer was concentrated
  3. customthen purified by chromatography on silica gel(chloroform/methanol)

Sources & evidence

ORD record
ord-6c03aa256d5e4a2a93719a4eb9aca3c6
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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