3,4-Diaminopyridine → 3-(3H-imidazo[4,5-c]pyridin-2-yl)-5-(4-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine

HRID 62097

Reaction equation

HRID 62097 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]2[C:16]([CH:17]=O)=[N:15][N:14]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[C:11]2=[N:12][CH:13]=1.[NH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[NH2:32].[S]>CN(C=O)C>[N:32]1[C:31]2[CH:30]=[CH:29][N:28]=[CH:27][C:26]=2[NH:25][C:17]=1[C:16]1[C:10]2[C:11](=[N:12][CH:13]=[C:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[CH:9]=2)[N:14]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[N:15]=1

Participants

5

Reactant 3

HCID 59183,4-DiaminopyridineHCID 5362487SulfurHCID 583780785-(4-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde

Product 1

HCID 1361935913-(3H-imidazo[4,5-c]pyridin-2-yl)-5-(4-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(4-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde (LVII) (0.120 g, 0.37 mmol), 3,4-diaminopyridine (LVIII) (42 mg, 0.39 mmol) and sulfur (13 mg, 0.39 mmol) in dry DMF (5 mL) was heated at 140° C. under nitrogen for 12 h. The solution was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was dissolved in DCM and washed with water (1×20 mL). The organic layer was dried over MgSO4, filtered and concentrated to yield 3-(3H-imidazo[4,5-c]pyridin-2-yl)-5-(4-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine (LIX). The crude product was used directly for step 3 without further purification. ESIMS found for C23H21N7O m/z 412.7 (M+H).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed with water (1×20 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-55b641bad9374ff2ba66f8c1660fc04f
Source dataset
uspto-grants-2016_09
Patent number
US09446035B2

Linked notes

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