Diisopropylethylamine → HCID 59164447, compound

HRID 1894128Notes

Reaction equation

HRID 1894128 reaction equation
CO[C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[N:12][CH:11]=2)[C:7]([CH:16]([CH3:18])[CH3:17])=[CH:6][C:5]=1[NH2:19].ClC([O:24][C:25]1C=CC(Cl)=CC=1)=O.[CH3:32][S:33]([NH:36][NH2:37])(=[O:35])=[O:34].CCN(C(C)C)C(C)C>O1CCOCC1>[CH:16]([C:7]1[CH:6]=[C:5]2[C:4]([C:3](=[O:20])[N:37]([NH:36][S:33]([CH3:32])(=[O:35])=[O:34])[C:25](=[O:24])[NH:19]2)=[CH:9][C:8]=1[C:10]1[CH:15]=[CH:14][N:13]=[N:12][CH:11]=1)([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 269268MethanesulfonohydrazideHCID 59164418HCID 59164418, compound

Product 1

HCID 59164447HCID 59164447, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-amino-4-isopropyl-5-pyridazin-4-yl-benzoic acid methyl ester (220 mg, 0.81 mmol) and 4-chlorophenyl chloroformate (170 μL, 1.22 mmol) in dioxane (10 mL) was stirred at r.t. for 10 min and at 80° C. for 30 min. After cooling to r.t., CH3SO2NHNH2 (178.6 mg, 1.6 mmol) and i-Pr2NEt (425 μL, 2.43 mmol) were added. The mixture was heated at 80° C. for 1.5 h, cooled to r.t., and the solvent was removed in vacuo. The residue was purified by flash chromatography (100 g silica gel, DCM→MeOH in DCM (2.5% to 5%)). The fractions containing the product were combined and concentrated in vacuo and the residue was further purified by trituration in MeOH-Et2O. After filtration and drying, the title compound (156 mg, 51%) was isolated as a white powder. API-ES: m/z 376 [M+H]+, rt 2.12 min.

Workup

  1. temperatureThe mixture was heated at 80° C. for 1.5 h
  2. temperaturecooled to r.t.
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by flash chromatography (100 g silica gel, DCM→MeOH in DCM (2.5% to 5%))
  5. additionThe fractions containing the product
  6. concentrationconcentrated in vacuo
  7. customthe residue was further purified by trituration in MeOH-Et2O
  8. filtrationAfter filtration
  9. customdrying

Sources & evidence

ORD record
ord-55bacf616ba54396a3a656c15d50292e
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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