HCID 178522041, compound → HCID 178522038, compound

HRID 1803500Notes

Reaction equation

HRID 1803500 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([OH:22])=[N:17][N:16]=[C:15]3Cl)=[O:11])[CH:6]=[CH:7][CH:8]=1>[Pd].CO>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([OH:22])=[N:17][N:16]=[CH:15]3)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 178522041HCID 178522041, compound

Product 1

HCID 178522038HCID 178522038, compoundYield 34.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-chloro-1-hydroxy-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (64 mg, 0.174 mmol) (example 25), MeOH (3 mL) and 10% wet Pd/C (catalytic) was evacuated and flushed (3×) with hydrogen. The mixture was stirred under hydrogen for 16 h. The mixture was filtered through celite, rinsed with MeOH and concentrated under vacuum. Chromatography (Hex/EtOAc) was used to obtain 1-hydroxy-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (20 mg) as a white solid. 1H NMR (400 MHz, CDCl3) δ: 7.35 (d, 1H), 7.45 (t, 1H), 8.03 (s, 1H), 8.08 (d, 1H), 8.19 (s, 1H), 8.30-8.37 (m, 2H), 8.44 (d, 1H), 10.05 (s, 1H), 11.26 (s, 1H) ppm. m/z 334.10.

Workup

  1. customwas evacuated
  2. customflushed (3×) with hydrogen
  3. filtrationThe mixture was filtered through celite
  4. washrinsed with MeOH
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e0fb302829e640f2864ad31fc7ad8909
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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