1-Methylhomopiperazine → HCID 10165194, compound

HRID 1373703Notes

Reaction equation

HRID 1373703 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][C:19](=[O:30])[C:20]2[CH:25]=[CH:24][C:23](F)=[CH:22][C:21]=2[O:27][CH2:28][CH3:29])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8].[CH3:31][N:32]1[CH2:38][CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>CS(C)=O.ClCCl>[CH2:28]([O:27][C:21]1[CH:22]=[C:23]([N:35]2[CH2:36][CH2:37][CH2:38][N:32]([CH3:31])[CH2:33][CH2:34]2)[CH:24]=[CH:25][C:20]=1[C:19]([NH:18][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:17][C:6]=1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8])=[O:30])[CH3:29]

Participants

5

Reactant 2

HCID 2283491-MethylhomopiperazineHCID 21075345HCID 21075345, compound

Product 1

HCID 10165194HCID 10165194, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

5-Fluoro-2-[4-fluoro-2-ethoxybenzoylamino]-N-(5-chloropyridin-2-yl)benzamide (135 mg, 0.31 mmol) and 1-methylhexahydro-1,4-diazepine (177 mg, 1.55 mmol, 5 eq) were dissolved in 250 μL DMSO, in a 4 mL screw cap vial. The pale yellow solution was incubated at 100° C. for 36–40 hours. The solution was cooled, diluted with 12 mL of dichloromethane, washed four times with water, once with brine, then dried over sodium sulfate and concentrated in vacuo. The crude residue was purified first by chromatography on a silica gel cartridge (2 g/12 cc, Varian Sample Preparation Products, Harbor City, Calif.) using zero to ten percent methanol in dichloromethane, then by radial chromatography with zero to ten percent methanol in dichloromethane. Pure fractions were pooled, concentrated in vacuo and dried under high vacuum to yield 107 mg (65%) of the title compound.

Workup

  1. customscrew cap vial
  2. waitThe pale yellow solution was incubated at 100° C. for 36–40 hours
  3. temperatureThe solution was cooled
  4. washwashed four times with water
  5. dry with materialonce with brine, then dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified first by chromatography on a silica gel cartridge (2 g/12 cc, Varian Sample Preparation Products, Harbor City, Calif.)
  8. concentrationconcentrated in vacuo
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-03b8a326f99b494c8a10c86839b771e3
Source dataset
uspto-grants-2007_01
Patent number
US07163938B2

Reaction notes

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