Dimethylformamide → HCID 22730625, compound

HRID 2085771Notes

Reaction equation

HRID 2085771 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=2)=[C:6]([O:20][CH3:21])[CH:5]=1.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.CN(C=[O:34])C>O.C(OCC)(=O)C>[CH3:21][O:20][C:6]1[CH:5]=[C:4]([CH2:3][C:2]([N:27]2[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]2)=[O:34])[CH:9]=[CH:8][C:7]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 531671-MethylpiperazineHCID 11531974HCID 11531974, compound

Product 1

HCID 22730625HCID 22730625, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 328A (213 mg, 0.5 mmol), 1-methylpiperazine (2.5 mmol), and bis(tricyclohexylphosphine)palladium chloride (0.0025 mmol) in DMF (1.5 mL) and water (0.25 mL) was heated to 80° C. for 8 hours, diluted with ethyl acetate (100 mL), washed with water (45 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 2-10% methanol/dichloromethane to provide the desired product.

Workup

  1. washwashed with water (45 mL) and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 2-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-3238d47daf30424e92c582dadb923cfb
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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