Diisopropylethylamine → HCID 11965616, compound

HRID 1894063Notes

Reaction equation

HRID 1894063 reaction equation
CO[C:3](=[O:30])[C:4]1[CH:9]=[C:8]([CH:10]2[CH2:14][CH2:13][O:12][CH2:11]2)[C:7]([C:15]([F:18])([F:17])[F:16])=[CH:6][C:5]=1[NH:19][C:20](OC1C=CC(Cl)=CC=1)=[O:21].[CH3:31][S:32]([NH:35][NH2:36])(=[O:34])=[O:33].CCN(C(C)C)C(C)C>O1CCOCC1>[O:21]=[C:20]1[N:36]([NH:35][S:32]([CH3:31])(=[O:34])=[O:33])[C:3](=[O:30])[C:4]2[C:5](=[CH:6][C:7]([C:15]([F:18])([F:17])[F:16])=[C:8]([CH:10]3[CH2:14][CH2:13][O:12][CH2:11]3)[CH:9]=2)[NH:19]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 269268MethanesulfonohydrazideHCID 11965615HCID 11965615, compound

Product 1

HCID 11965616HCID 11965616, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2-(4-Chloro-phenoxycarbonylamino)-5-(tetrahydro-furan-3-yl)-4-trifluoromethyl-benzoic acid methyl ester (80 mg, 0.18 mmol) was dissolved in dioxane (1 mL) and, after addition of CH3SO2NHNH2 (21.8 mg, 1.1 equiv) and i-Pr2NEt (61.7 μL, 2 equiv), the mixture was stirred for 18 h (TLC control) at 80° C. The crude product was purified by flash chromatography with DCM to DCM/MeOH 85:15 as eluent. The obtained product was dried, dissolved in a small quantity of DCM and precipitated with hexanes. The white solid was filtered off and dried to provide the title compound (50 mg, 70% yield) (394 [M+H]+, rt 4.58 min.).

Workup

  1. customThe crude product was purified by flash chromatography with DCM to DCM/MeOH 85:15 as eluent
  2. customThe obtained product was dried
  3. dissolutiondissolved in a small quantity of DCM
  4. customprecipitated with hexanes
  5. filtrationThe white solid was filtered off
  6. customdried

Sources & evidence

ORD record
ord-c7dfdf95330744c4b15d4a739cfe7f46
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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