3-(aminomethyl)-6-methyl-4-(phenylmethyl)-2(1H)-pyridinone → N-((4-benzyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522537Notes

Reaction equation

HRID 1522537 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([C:11]([OH:13])=O)=[CH:8][CH:7]=[N:6][C:5]=2[N:4]([CH:14]([CH3:16])[CH3:15])[N:3]=1.[NH2:17][CH2:18][C:19]1[C:20](=[O:33])[NH:21][C:22]([CH3:32])=[CH:23][C:24]=1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:25]([C:24]1[CH:23]=[C:22]([CH3:32])[NH:21][C:20](=[O:33])[C:19]=1[CH2:18][NH:17][C:11]([C:9]1[C:10]2[C:2]([CH3:1])=[N:3][N:4]([CH:14]([CH3:16])[CH3:15])[C:5]=2[N:6]=[CH:7][CH:8]=1)=[O:13])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 674636783-(aminomethyl)-6-methyl-4-(phenylmethyl)-2(1H)-pyridinoneHCID 895439301-isopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 89467175N-((4-benzyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Procedure

The title compound was prepared in the same manner as described for example 11 from 3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.060 g, 0.274 mmol) and 3-(aminomethyl)-6-methyl-4-(phenylmethyl)-2(1H)-pyridinone (0.076 g, 0.287 mmol). The product was collected as a white solid (92 mg, 77%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46 (d, J=6.82 Hz, 6 H), 2.09 (s, 3 H), 2.41 (s, 3 H), 3.98 (s, 2 H), 4.43 (d, J=5.05 Hz, 2 H), 5.16 (quin, J=6.63 Hz, 1 H), 5.79 (s, 1 H), 7.04 (d, J=4.80 Hz, 1 H), 7.16-7.34 (m, 5 H), 8.49 (d, J=4.55 Hz, 1 H), 8.75 (t, J=5.05 Hz, 1 H), 11.59 (s, 1 H). LCMS(ES) [M+H]+ 429.9

Workup

  1. customThe product was collected as a white solid (92 mg, 77%)

Sources & evidence

ORD record
ord-c460eadbac95482d97bb2904eff84129
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

Loading…