HCID 178526564, compound → HCID 178507463, compound

HRID 2183137Notes

Reaction equation

HRID 2183137 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[NH:18][C:19]([C:22]5[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=5)=[N:20][N:21]=4)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[NH:18][C:19]([C:22]5[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=5)=[N:20][N:21]=4)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 178526564HCID 178526564, compound

Product 1

HCID 178507463HCID 178507463, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing 5-[3-(4-fluorophenyl)(1H-indazol-5-yl)]-3-(4-nitrophenyl)-4H-1,2,4-triazole (60 mg) was added ethyl acetate (15 ml). The flask was evacuated and purged with nitrogen. To the flask was added palladium on carbon catalyst (10 mg). The reaction was placed under a hydrogen atmosphere and allowed to stir overnight. The reaction was filtered through celite and the organic layer was concentrated. The product was purified by HPLC to yield the title compound (15 mg, 26% yield). 1H NMR (DMSO-d6) δ 13.5 (s, 1H), 8.65 (s, 1H), 8.1 (d, 1H), 8.05 (t, 2H), 7.77 (d, 2H), 7.7 (d, 1H), 7.4 (t, 2H), 6.7 (d, 2H), ES-MS (m/z) 371 [M+1]+.

Workup

  1. customThe flask was evacuated
  2. custompurged with nitrogen
  3. additionTo the flask was added palladium on carbon catalyst (10 mg)
  4. filtrationThe reaction was filtered through celite
  5. concentrationthe organic layer was concentrated
  6. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-f939a3670e8a413d8695dfb6900a4421
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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