HCID 86675992, compound → HCID 86675991, compound

HRID 1253406Notes

Reaction equation

HRID 1253406 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([CH2:19][CH3:20])[C:4]=1[NH:21][C:22](=[O:37])[C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH:33]=[N:32][CH:31]=[N:30]2)=[C:25]([N+:34]([O-])=O)[CH:24]=1)[CH3:2]>C(O)C.[Pd]>[NH2:34][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[N:29]1[CH:33]=[N:32][CH:31]=[N:30]1)[C:22]([NH:21][C:4]1[C:5]([CH2:19][CH3:20])=[CH:6][C:7]([C:9]([F:18])([C:10]([F:11])([F:12])[F:13])[C:14]([F:16])([F:17])[F:15])=[CH:8][C:3]=1[CH2:1][CH3:2])=[O:37]

Participants

4

Reactant 1

HCID 86675992HCID 86675992, compound

Product 1

HCID 86675991HCID 86675991, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-[2,6-diethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethylethyl)phenyl]-3-nitro-4-(1,2,4-triazol-1-yl)benzamide (473 mg, 0.89 mmol) (Example I2) in ethanol (9 ml) was charged with palladium on carbon (10%) (140 mg, 0.13 mmol) and was stirred under a atmosphere of hydrogen for 15 hours. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:4) to give Compound No. B2 of Table B (328 mg, 74% yield) and Compound No. C1 of Table C (18 mg, 4% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:4)
  4. customto give Compound No

Sources & evidence

ORD record
ord-4ed8b6231e6b40bbb1e175a4a6e4f7a1
Source dataset
uspto-grants-2013_06
Patent number
US08455399B2

Reaction notes

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