4-Aminopyridine → HCID 56598681, compound

HRID 476012Notes

Reaction equation

HRID 476012 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.[N:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[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:33][C:30]2[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=2)[CH:3]=1)=[O:15]

Participants

7

Reactant 4

HCID 17274-AminopyridineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-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 56598681HCID 56598681, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared in the same manner as described in example 74 using 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 (50 mg, 0.134 mmol), 4-pyridinamine (12.59 mg, 0.134 mmol), cesium carbonate (131 mg, 0.401 mmol), 1,4-dioxane (2 mL), palladium(II) acetate (1.501 mg, 6.69 μmol) and BINAP (8.33 mg, 0.013 mmol), wherein the reaction time was 2 h. The final product was collected as 29 mg (50%). LCMS E-S (M+H)=432.3 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45-1.59 (d, J=6.8 Hz, 6H), 2.14 (s, 3H), 2.23 (s, 3H), 4.36 (d, J=5.0 Hz, 2H), 5.16 (m, 1H), 5.91 (s, 1H), 7.09 (s, 1H), 7.99 (d, J=6.1 Hz, 2H), 8.12 (s, 1H) 8.49 (d, J=6.6 Hz, 2H), 8.74 (t, J=5.1 Hz, 1H), 10.58 (s, 1H), 11.58 (s, 1H).

Workup

  1. customThe final product was collected as 29 mg (50%)

Sources & evidence

ORD record
ord-52ad821a648247a7bee29e40e9e53195
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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