HCID 24947400, compound → HCID 24947399, compound

HRID 1803485Notes

Reaction equation

HRID 1803485 reaction equation
[F:1][C:2]([F:32])([F:31])[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]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:17][N:16]=[C:15]3I)=[O:11])[CH:6]=[CH:7][CH:8]=1>[Pd].CO>[F:32][C:2]([F:1])([F:31])[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]([NH:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:17][N:16]=[CH:15]3)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 24947400HCID 24947400, compound

Product 1

HCID 24947399HCID 24947399, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-benzylamino-4-iodo-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (24 mg, 0.04 mmol), MeOH (5 mL) and 10% wet Pd/C (catalytic) was evacuated and flushed (3×) with hydrogen. The mixture was stirred under hydrogen for 5 hours. The mixture was filtered through celite, rinsed with MeOH and concentrated under vacuum. Chromatography (hexanes/EtOAc) was used to obtain 1-Benzylamino-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (9 mg, 50%) as a solid, 1H-NMR (CDCl3) δ: 4.80 (bs, 2H), 7.35 (m, 7H), 8.10 (m, 3H), 8.30 (bs, 2H), 8.80 (bs, 1H). m/z (M+1) 423.23.

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-9cfefa06cb094f3faa6f0521fe71551c
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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