Ethanolamine → HCID 56598280, compound

HRID 1522392Notes

Reaction equation

HRID 1522392 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][OH:30]>CN1C(=O)CCC1>[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:27][CH2:28][CH2:29][OH:30])[CH:3]=1)=[O:15]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 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 56598280HCID 56598280, compoundYield 63%

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-aminoethanol (1 ml) in NMP (2 mL). The vessel was sealed and the reaction mixture was irradiated (microwave) at 130° C. for 1 h and then at 140° C. for 90 min. The mixture was evaporated under vacuum and 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, sonicated, and treated with hexanes. The solids were filtered, dissolved in DMF (1 mL), and a few drops of water were added. The solution was allowed to stand at room temperature overnight, and then sonicated. The filtered solid was washed with Hexanes/EtOAc (1:1), and then dried to afford the title compound (55 mg, 63%) as a light yellow solid. LCMS E-S (M+H)=399.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.56 (br. s., 1 H) 8.44 (br. s., 1 H) 7.84 (s, 1 H) 7.20 (br. s., 1 H) 6.68 (s, 1 H) 5.89 (s, 1 H) 4.95 (dt, J=13.01, 6.38 Hz, 1 H) 4.72 (t, J=4.93 Hz, 1 H) 4.32 (d, J=4.80 Hz, 2 H) 3.58 (d, J=5.56 Hz, 2 H) 3.38-3.46 (m, 2 H) 2.21 (s, 3 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 130° C. for 1 h
  4. customThe mixture was evaporated under vacuum
  5. customthe residue was purified by silica gel chromatography (eluent: gradient 0 to 90:10:1 DCM/MeOH/NH4OH)
  6. additionThe isolated yellow oil was treated with EtOAc
  7. customsonicated
  8. additiontreated with hexanes
  9. filtrationThe solids were filtered
  10. dissolutiondissolved in DMF (1 mL)
  11. additiona few drops of water were added
  12. waitto stand at room temperature overnight
  13. customsonicated
  14. washThe filtered solid was washed with Hexanes/EtOAc (1:1)
  15. customdried

Sources & evidence

ORD record
ord-e7bd6c3fc4044c06a55ae8ce8c15204b
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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