1-(1-Methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid → 1-(1-Methylethyl)-N-[(6-methyl-2-oxo-4-phenyl-1,2-dihydro-3-pyridinyl)methyl]-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522353Notes

Reaction equation

HRID 1522353 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:11]=[C:12]([C:13](O)=[O:14])[C:7]=2[CH:6]=[N:5]1)[CH3:3].[NH2:22][CH2:23][C:24]1[C:25](=[O:37])[NH:26][C:27]([CH3:36])=[CH:28][C:29]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:11]=[C:12]([C:13]([NH:22][CH2:23][C:24]3[C:25](=[O:37])[NH:26][C:27]([CH3:36])=[CH:28][C:29]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:14])[C:7]=2[CH:6]=[N:5]1)[CH3:3]

Participants

3

Reactant 2

HCID 201146251-(1-Methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidHCID 671242923-(Aminomethyl)-6-methyl-4-phenyl-2(1H)-pyridinone

Product 1

HCID 712812041-(1-Methylethyl)-N-[(6-methyl-2-oxo-4-phenyl-1,2-dihydro-3-pyridinyl)methyl]-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Procedure

The title compound was prepared in the same manner as described in example 11 from 1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (150 mg, 0.531 mmol) and 3-(aminomethyl)-6-methyl-4-phenyl-2(1H)-pyridinone (133 mg, 0.531 mmol). The product was collected as a white solid, 0.041 g (15%). LCMS E-S (M+H)=479.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (d, J=6.82 Hz, 6 H) 2.23 (s, 3 H) 4.23-4.27 (m, 2 H) 5.33-5.42 (m, 1 H) 6.02-6.04 (m, 1 H) 7.35-7.42 (m, 1 H) 7.43 (s, 4 H) 8.23-8.26 (m, 1 H) 8.34-8.39 (m, 2 H) 8.41-8.42 (m, 1 H) 8.84-8.88 (m, 2 H) 8.91-8.96 (m, 1 H) 11.91 (s, 1 H).

Workup

  1. customThe product was collected as a white solid, 0.041 g (15%)

Sources & evidence

ORD record
ord-af8b014009ae4c9dbab96f2050e391d6
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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