HCID 90411382, compound → HCID 90410906, compound

HRID 627065Notes

Reaction equation

HRID 627065 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:15][CH2:14][C:13]2[C:12]3[NH:16][C:17](C(O)=O)=[CH:18][C:11]=3[S:10][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]>CN1C(=O)CCC1.O.[Cu]>[CH2:1]([O:3][C:4]([N:6]1[CH2:15][CH2:14][C:13]2[C:12]3[NH:16][CH:17]=[CH:18][C:11]=3[S:10][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 90411382HCID 90411382, compound

Product 1

HCID 90410906HCID 90410906, compoundYield 93.4%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
250 °C

Procedure

To a stirred solution of the product from step (f) (0.50 g, 1.62 mmol) in NMP (10 ml) was added copper dust (0.10 g, 1.62 mmol). The reaction mixture was heated in a microwave reactor to 250° C. for 20 minutes. The cooled solution was diluted with water (100 ml) and extracted with Et2O (3×). The combined Et2O extracts were washed with brine, dried (MgSO4), filtered, and solvent evaporated in vacuo to give the crude product. Purification by silica-gel chromatography (gradient elution: 0 to 100% EtOAc in hexanes gave the sub-titled compound as a tan solid (0.40 g). MS: ESI (positive): 265 (M+H).

Workup

  1. extractionextracted with Et2O (3×)
  2. washThe combined Et2O extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customsolvent evaporated in vacuo
  6. customto give the crude product
  7. customPurification by silica-gel chromatography (
  8. washgradient elution

Sources & evidence

ORD record
ord-d878d52a0e3349ebbed19aee7b0f51f5
Source dataset
uspto-grants-2016_04
Patent number
US09309262B2

Reaction notes

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