N,N-Dimethylethylenediamine → HCID 56598279, compound

HRID 1522391Notes

Reaction equation

HRID 1522391 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.[NH2:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31]>CN1C(=O)CCC1>[CH3:31][N:30]([CH3:32])[CH2:29][CH2:28][NH:27][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

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 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 56598279HCID 56598279, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 25 mL sealable tube under nitrogen were combined 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 (80 mg, 0.21 mmol) and (2-aminoethyl)dimethylamine (37.7 mg, 0.43 mmol) in NMP (2 mL). The vessel was sealed and the reaction mixture was irradiated (microwave) at 150° C. for 1 h. The mixture was evaporated under vacuum, and the resulting residue was partitioned between EtOAc and water. The contents were extracted with EtOAc, DCM and DCM/isopropanol (70:30). The combined organics were washed with water (2×) and brine, dried over MgSO4, filtered and evaporated. The residue was purified by silica gel chromatography (eluent: gradient 0 to 90:10:1 DCM/MeOH/NH4OH). The isolated yellow oil was treated with EtOAc and sonicated. Solids that precipitated were filtered, washed with hexanes, and dried to afford the title compound (60 mg, 65%) as a white solid. LCMS E-S (M+H)=425.9. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.55 (br. s., 1 H) 8.43 (t, J=5.05 Hz, 1 H) 7.84 (s, 1 H) 7.08 (t, J=5.05 Hz, 1 H) 6.67 (s, 1 H) 5.89 (s, 1 H) 4.94 (quin, J=6.63 Hz, 1 H) 4.32 (d, J=5.05 Hz, 2 H) 3.44 (q, J=6.48 Hz, 2 H) 2.44 (t, J=6.69 Hz, 2 H) 2.17-2.22 (m, 9 H) 2.12 (s, 3 H) 1.43 (d, J=6.57 Hz, 6 H).

Workup

  1. customIn a 25 mL sealable tube under nitrogen were combined
  2. customThe vessel was sealed
  3. customthe reaction mixture was irradiated (microwave) at 150° C. for 1 h
  4. customThe mixture was evaporated under vacuum
  5. customthe resulting residue was partitioned between EtOAc and water
  6. extractionThe contents were extracted with EtOAc, DCM and DCM/isopropanol (70:30)
  7. washThe combined organics were washed with water (2×) and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by silica gel chromatography (eluent: gradient 0 to 90:10:1 DCM/MeOH/NH4OH)
  12. additionThe isolated yellow oil was treated with EtOAc
  13. customsonicated
  14. customSolids that precipitated
  15. filtrationwere filtered
  16. washwashed with hexanes
  17. customdried

Sources & evidence

ORD record
ord-65870a658bff46ee912cb8aea345d5f8
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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