3-(3-(1-benzyl-1H-pyrazol-4-yl)pyridin-2-yloxy)-N-(3-isopropylphenyl)-4-methylbenzamide → 3-(3-(1H-pyrazol-4-yl)pyridin-2-yloxy)-N-(3-isopropylphenyl)-4-methylbenzamide

HRID 883028Notes

Reaction equation

HRID 883028 reaction equation
C([N:8]1[CH:12]=[C:11]([C:13]2[C:14]([O:19][C:20]3[CH:21]=[C:22]([CH:35]=[CH:36][C:37]=3[CH3:38])[C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]([CH3:34])[CH3:33])[CH:27]=3)=[O:24])=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:10]=[N:9]1)C1C=CC=CC=1>CCOC(C)=O.CO.[Pd]>[NH:8]1[CH:12]=[C:11]([C:13]2[C:14]([O:19][C:20]3[CH:21]=[C:22]([CH:35]=[CH:36][C:37]=3[CH3:38])[C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]([CH3:34])[CH3:33])[CH:27]=3)=[O:24])=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:10]=[N:9]1

Participants

5

Reactant 1

HCID 251022303-(3-(1-benzyl-1H-pyrazol-4-yl)pyridin-2-yloxy)-N-(3-isopropylphenyl)-4-methylbenzamide

Product 1

HCID 251020863-(3-(1H-pyrazol-4-yl)pyridin-2-yloxy)-N-(3-isopropylphenyl)-4-methylbenzamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-(3-(1-benzyl-1H-pyrazol-4-yl)pyridin-2-yloxy)-N-(3-isopropylphenyl)-4-methylbenzamide (65 mg, 0.13 mmol) in EtOAc (4 mL) and MeOH (4 mL) was added Pd/C (10%, 300 mg). The reaction was purged with hydrogen gas and then stirred at rt under a balloon of hydrogen for 16 hours. The reaction was filtered through Celite with EtOAc, concentrated, and purified by Gilson reverse-phase HPLC (0.1% TFA in water/acetonitrile). After a basic workup involving CH2Cl2 and saturated sodium bicarbonate, 3-(3-(1H-pyrazol-4-yl)pyridin-2-yloxy)-N-(3-isopropylphenyl)-4-methylbenzamide was obtained as a white solid. MS m/z=413 [M+1]+. Calc'd for C25H24N4O2: 412.50.

Workup

  1. customThe reaction was purged with hydrogen gas
  2. filtrationThe reaction was filtered through Celite with EtOAc
  3. concentrationconcentrated
  4. custompurified by Gilson reverse-phase HPLC (0.1% TFA in water/acetonitrile)

Sources & evidence

ORD record
ord-14a4d7d9093d4a4cbbe5665083dc4f53
Source dataset
uspto-grants-2012_08
Patent number
US08236823B2

Reaction notes

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