HCID 178513739, compound → HCID 178513736, compound

HRID 527261Notes

Reaction equation

HRID 527261 reaction equation
[OH:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]2[NH:12][N:11]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=3)[C:9]=2[C:23]([NH2:25])=[O:24])=[CH:4][CH:3]=1>CO.[Pd]>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:10]2[C:9]([C:23]([NH2:25])=[O:24])=[C:8]([NH:7][CH2:6][C:5]3[CH:26]=[CH:27][C:2]([OH:1])=[CH:3][CH:4]=3)[NH:12][N:11]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 178513739HCID 178513739, compound

Product 1

HCID 178513736HCID 178513736, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-((4-hydroxybenzyl)amino)-3-((4-nitrophenyl)amino)-1H-pyrazole-4-carboxamide (4.80 g) was suspended in 300 mL of MeOH and palladium on carbon (50% wet with water) (480 mg, 0.10 eq.) was then added to the reaction vessel. The reaction was then purged and stirred under hydrogen pressure at room temperature for 18 hrs. or until no starting material is present and confirmed via HPLC. Once complete Celite was stirred into the reaction vessel, filtered through Celite and washed with additional MeOH. The MeOH was then evaporated off via vacuo and triturated with ethyl acetate and hexanes to yield 3-((4-aminophenyl)amino)-5-((4-hydroxybenzyl)amino)-1H-pyrazole-4-carboxamide as a light purple powder collected via filtration (1.60 g, 36% yield).

Workup

  1. customThe reaction was then purged
  2. stirringOnce complete Celite was stirred into the reaction vessel
  3. filtrationfiltered through Celite
  4. washwashed with additional MeOH
  5. customThe MeOH was then evaporated off via vacuo
  6. customtriturated with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-99d830e0c5cd4916ae66b8ad7145d835
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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