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Methanesulfonic Acid → 6-Amino-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522347
Notes
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Reaction equation

HRID 1522347 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[C:15]2[CH:26]=[N:25][N:24]([CH:27]([CH3:29])[CH3:28])[C:16]=2[N:17]=[C:18]([NH:20]CC=C)[CH:19]=1)=[O:13].CS(O)(=O)=O>C(O)C.C(Cl)Cl.[Pd]>[NH2:20][C:18]1[CH:19]=[C:14]([C:12]([NH:11][CH2:10][C:3]2[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[O:13])[C:15]2[CH:26]=[N:25][N:24]([CH:27]([CH3:29])[CH3:28])[C:16]=2[N:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 6395Methanesulfonic AcidHCID 56597559N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(2-propen-1-ylamino)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Product 1

HCID 565975586-Amino-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst
HCID 702
Ethanol
Solvent
HCID 6344DichloromethaneSolvent

Procedure

A mixture of 10% Pd/C (0.200 g, 0.188 mmol) and N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(2-propen-1-ylamino)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.200 g, 0.507 mmol) was suspended in ethanol (10 mL) and stirred. Added next was methanesulfonic acid (0.033 mL, 0.507 mmol), and the stirring contents were heated at reflux for 2 h. After cooling to room temperature, the reaction mixture was diluted with DCM and filtered through Celite. The filter pad was washed with 10% MeOH/DCM. The filtrate was pre-adsorped onto silica gel, and the crude product purified by silica gel chromatography (dry loaded, eluent: gradient of 5-80% Dichloromethane/Chloroform containing 10% 2M Ammonia (in methanol)). The collected product was dried in vacuum oven at 45° C. overnight. The final product was collected as 0.065 g (36%). LCMS E-S (M+H)=355.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.40 (d, J=6.82 Hz, 6 H), 2.12 (s, 3 H), 2.21 (s, 3 H), 4.31 (d, J=5.05 Hz, 2 H), 4.85-5.00 (m, 1 H), 5.89 (s, 1H), 6.49-6.68 (m, 3 H), 7.85 (s, 1 H), 8.46 (t, J=5.05 Hz, 1 H), 11.54 (br. s., 1 H).

Workup

  1. additionAdded next
  2. temperaturethe stirring contents were heated
  3. temperatureat reflux for 2 h
  4. filtrationfiltered through Celite
  5. washThe filter pad was washed with 10% MeOH/DCM
  6. customthe crude product purified by silica gel chromatography (dry loaded, eluent: gradient of 5-80% Dichloromethane/Chloroform containing 10% 2M Ammonia (in methanol))
  7. customThe collected product was dried in vacuum oven at 45° C. overnight
  8. customThe final product was collected as 0.065 g (36%)

Sources & evidence

ORD record
ord-1f2ff11d17ae40a5a6e86651615a85e2
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073924B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes