Diisopropylethylamine → HCID 11965785, compound

HRID 1441649Notes

Reaction equation

HRID 1441649 reaction equation
CO[C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=2)[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:6][C:5]=1[NH2:20].ClC([O:25][C:26]1C=CC(Cl)=CC=1)=O.[CH3:33][S:34]([NH:37][NH2:38])(=[O:36])=[O:35].CCN(C(C)C)C(C)C>O1CCOCC1>[O:25]=[C:26]1[N:38]([NH:37][S:34]([CH3:33])(=[O:36])=[O:35])[C:3](=[O:21])[C:4]2[C:5](=[CH:6][C:7]([C:16]([F:18])([F:19])[F:17])=[C:8]([C:10]3[CH:11]=[N:12][CH:13]=[N:14][CH:15]=3)[CH:9]=2)[NH:20]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 269268MethanesulfonohydrazideHCID 11965784HCID 11965784, compound

Product 1

HCID 11965785HCID 11965785, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-amino-5-pyrimidin-5-yl-4-trifluoromethyl-benzoic acid methyl ester (518 mg, 1.74 mmol) and 4-chlorophenyl chloroformate (244 μL, 1.74 mmol) in dioxane (8 mL) was stirred at 80° C. for 2 h. After cooling to r.t., CH3SO2NHNH2 (230.4 mg, 2.1 mmol) and i-Pr2NEt (609 μL, 3.49 mmol) were added. The mixture was heated to 80° C. for 4 h and, cooled to r.t., and the solvent was removed in vacuo. The residue was purified by flash chromatography (120 g silica gel, DCM→MeOH in DCM (2% to 5%)). The product was sonicated in MeOH/Et2O to furnish the title compound (252 mg, 36%) as a beige powder. API-ES: m/z 402 [M+H]+, rt 2.52 min.

Workup

  1. temperatureThe mixture was heated to 80° C. for 4 h
  2. temperaturecooled to r.t.
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by flash chromatography (120 g silica gel, DCM→MeOH in DCM (2% to 5%))
  5. customThe product was sonicated in MeOH/Et2O

Sources & evidence

ORD record
ord-1bc5b4c65d0e4bdd92e2984060d651f3
Source dataset
uspto-grants-2010_02
Patent number
US07655666B2

Reaction notes

Loading…