HCID 86670241, compound → HCID 178441083, compound

HRID 872572Notes

Reaction equation

HRID 872572 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([NH:12][NH2:13])=[O:11])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:14]([C:16]1[O:20][C:19]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([C:29]([F:32])([F:31])[F:30])[CH:22]=2)=[CH:18][CH:17]=1)=O.C(O)C>>[C:1]([C:5]1[CH:9]=[C:8]([C:10](/[N:12]=[N:13]/[CH2:14][C:16]2[O:20][C:19]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([C:29]([F:32])([F:30])[F:31])[CH:22]=3)=[CH:18][CH:17]=2)=[O:11])[NH:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 86670241HCID 86670241, compoundHCID 178441084HCID 178441084, compound

Product 1

HCID 178441083HCID 178441083, compound

Procedure

To the solution of 3-tert-butyl-1H-pyrazole-5-carbohydrazide (0.076 g, 0.41 mmol) in 10 ml of ethanol 4-(5-formylfuran-2-yl)-2-(trifluoromethyl)benzonitrile (0.10 g, 0.37 mmol) was added and the mixture was stirred at RT for 36 h. The solvent was evaporated and the residue purified with Combiflash using DCM/-methanol as eluent system affording fractions containing the title compound. After treatment of these fractions with DCM the product precipitated out producing 0.048 g of title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.31 (s, 9H), 6.55 (m, 1H), 7.12 (d, 1H), 7.65 (d, 1H), 8.24 (m, 2H), 8.28 (m, 1H), 8.48 (m, 1H), 11.82 (m, 1H), 13.07 (m, 1H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified with Combiflash
  3. customaffording fractions

Sources & evidence

ORD record
ord-8962e7c7578b44dab59cf41e0acb10bd
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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