Benzamide → HCID 21075339, compound

HRID 1373707Notes

Reaction equation

HRID 1373707 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][C:19](=[O:32])[C:20]2[CH:25]=[CH:24][C:23](F)=[CH:22][C:21]=2[O:27][CH2:28][CH2:29][S:30][CH3:31])=[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].[CH3:33][N:34]1[CH2:40][CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(N)(=O)C1C=CC=CC=1>CS(C)=O.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][C:19](=[O:32])[C:20]2[CH:25]=[CH:24][C:23]([N:37]3[CH2:38][CH2:39][CH2:40][N:34]([CH3:33])[CH2:35][CH2:36]3)=[CH:22][C:21]=2[O:27][CH2:28][CH2:29][S:30][CH3:31])=[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]

Participants

6

Reactant 3

HCID 2331BenzamideHCID 2283491-MethylhomopiperazineHCID 21075343HCID 21075343, compound

Product 1

HCID 21075339HCID 21075339, compoundYield 117.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

In a 4 mL screw-cap vial were dissolved 5-fluoro-2-[4-fluoro-2-(2-methylthioethoxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide (131 mg, 274 μmol) and 1-methylhexahydro-1,4-diazepine (157 mg, 1.37 mmol, 5 eq) in 250 μL DMSO to give a light yellow solution. The solution was heated to 100° C. for 36 hours in a heatblock, then allowed to cool to room temperature. The resulting brown solution was diluted with 1 mL dichloromethane, washed four times with water, once with brine, then dried over sodium sulfate and concentrated. The residue was combined with that from a separate, smaller scale run (100 μmol of starting benzamide) and purified via radial chromatography with 95:5, then 9:1 dichloromethane:methanol to produce 184 mg (86%) of the title compound as a yellow oil.

Workup

  1. customIn a 4 mL screw-cap vial
  2. customto give a light yellow solution
  3. temperatureto cool to room temperature
  4. washwashed four times with water
  5. dry with materialonce with brine, then dried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified via radial chromatography with 95:5

Sources & evidence

ORD record
ord-c7f090a8f93144fd80263153c90c2155
Source dataset
uspto-grants-2007_01
Patent number
US07163938B2

Reaction notes

Loading…