Nitrogen → 2-[2-(2,5-Dimethyl-2H-pyrazol-3-ylamino)-5-isopropyl-pyridin-4-ylamino]-N-methyl-benzamide

HRID 62518Notes

Reaction equation

HRID 62518 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8]2[CH:13]=[C:12]([NH:14][C:15]3[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=3[C:17]([NH:19][CH3:20])=[O:18])[C:11]([C:25]([CH3:27])=[CH2:26])=[CH:10][N:9]=2)=[CH:5][C:4]([CH3:28])=[N:3]1.N#N>C(O)C.O=[Pt]=O>[CH3:1][N:2]1[C:6]([NH:7][C:8]2[CH:13]=[C:12]([NH:14][C:15]3[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=3[C:17]([NH:19][CH3:20])=[O:18])[C:11]([CH:25]([CH3:26])[CH3:27])=[CH:10][N:9]=2)=[CH:5][C:4]([CH3:28])=[N:3]1

Participants

5

Reactant 2

HCID 947NitrogenHCID 462152722-[2-(2,5-Dimethyl-2H-pyrazol-3-ylamino)-5-isopropenyl-pyridin-4-ylamino]-N-methyl-benzamide

Product 1

HCID 545889872-[2-(2,5-Dimethyl-2H-pyrazol-3-ylamino)-5-isopropyl-pyridin-4-ylamino]-N-methyl-benzamideYield 61.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-[2-(2,5-dimethyl-2H-pyrazol-3-ylamino)-5-isopropenyl-pyridin-4-ylamino]-N-methyl-benzamide (0.13 g, 0.345 mmole, 1 eq) in ethanol (10 mL) was degassed with N2 and to this PtO2(0.012 g, 0.052 mmole, 0.15 eq) was added. The resulting mixture was stirred at room temperature under H2 atmosphere with balloon pressure for 10 h. After completion of the reaction, it was filtered through a celite bed which was then washed with ethanol (10 mL). The filtrate was evaporated under reduced pressure to give a solid residue which was purified by washing with diethyl ether to give the title compound as a gray solid (80 mg, 61%). 1H-NMR (400 MHz, DMSO-d6): δ 1.24-1.26 (d, 6H, J=6.76 Hz), 2.05 (s, 3H), 2.75-2.76 (d, 3H, J=4.48 Hz), 2.89-3.10 (m, 1H), 3.53 (s, 3H), 5.96 (s, 1H), 6.67 (s, 1H), 6.85-7.10 (m, 1H), 7.40-7.50 (m, 2H), 7.65-7.67 (d, 1H, J=7.76 Hz), 7.86 (s, 1H), 8.36 (s, 1H), 8.60-8.70 (brs, 1H), 9.89 (s, 1H). LC-MS [M+H]+=379.2.

Workup

  1. additionwas added
  2. customAfter completion of the reaction, it
  3. filtrationwas filtered through a celite bed which
  4. washwas then washed with ethanol (10 mL)
  5. customThe filtrate was evaporated under reduced pressure
  6. customto give a solid residue which
  7. customwas purified
  8. washby washing with diethyl ether

Sources & evidence

ORD record
ord-f7434a9b26d84522a4260371a875a3c2
Source dataset
uspto-grants-2016_09
Patent number
US09446034B2

Reaction notes

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