Ethylamine → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-(ethylamino)-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 475968

Reaction equation

HRID 475968 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.[CH2:27]([NH2:29])[CH3:28]>C(O)C>[CH3:24][C:23]1[CH:22]=[C:21]([CH3:25])[NH:20][C:19](=[O:26])[C:18]=1[CH2:17][NH:16][C:14]([C:4]1[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=[C:2]([NH:29][CH2:27][CH3:28])[CH:3]=1)=[O:15]

Participants

4

Reactant 2

HCID 6341Ethylamine2×HCID 565974256-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Product 1

HCID 56597706N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-(ethylamino)-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 10 mL microwave vial equipped with stir bar, septum cap and nitrogen inlet were added 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (23 mg, 0.062 mmol) and ethanol (1 mL). Added next to the stirring suspension was ethylamine (0.100 mL, 1.230 mmol) via syringe at once. The sealed reaction mixture was irradiated (microwave) at 110° C. for 40 min, followed by addition of 0.1 mL ethylamine and further irradiation for 7 hr at 130° C. After cooling to room temperature, about 50% of the volatiles were removed by a stream of nitrogen. The reaction mixture was diluted with water (20 mL) and stirred for 10 min. The mixture was then filtered and the collected solid washed with water. The solid was dried in vacuum oven at 50° C. for 18 h, to afford the title compound as 0.17 g (71%). LCMS E-S (M+H)=383.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.17 (t, J=7.07 Hz, 3H), 1.43 (d, J=6.57 Hz, 6H), 2.12 (s, 3H), 2.21 (s, 3H), 3.35-3.39 (m, 2H), 4.31 (d, J=5.05 Hz, 2H), 4.89-5.01 (m, 1H), 5.89 (s, 1H), 6.61 (s, 1H), 7.18 (t, J=5.31 Hz, 1H), 7.83 (s, 1H), 8.44 (t, J=5.05 Hz, 1H), 11.55 (br. s., 1H).

Workup

  1. customTo a 10 mL microwave vial equipped
  2. customseptum cap
  3. additionAdded next to the stirring suspension
  4. customThe sealed reaction mixture
  5. customwas irradiated (microwave) at 110° C. for 40 min
  6. customabout 50% of the volatiles were removed by a stream of nitrogen
  7. additionThe reaction mixture was diluted with water (20 mL)
  8. stirringstirred for 10 min
  9. filtrationThe mixture was then filtered
  10. washthe collected solid washed with water
  11. customThe solid was dried in vacuum oven at 50° C. for 18 h

Sources & evidence

ORD record
ord-c80863085089426ca74ac3a287fa1d67
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Linked notes

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