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

HRID 1522535Notes

Reaction equation

HRID 1522535 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[CH:10][CH:11]=[C:12]([C:13]([OH:15])=O)[C:7]=2[CH:6]=[N:5]1)[CH3:3].[NH2:16][CH2:17][C:18]1[C:19](=[O:32])[NH:20][C:21]([CH3:31])=[CH:22][C:23]=1[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([C:23]1[CH:22]=[C:21]([CH3:31])[NH:20][C:19](=[O:32])[C:18]=1[CH2:17][NH:16][C:13]([C:12]1[C:7]2[CH:6]=[N:5][N:4]([CH:2]([CH3:1])[CH3:3])[C:8]=2[N:9]=[CH:10][CH:11]=1)=[O:15])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 674636783-(aminomethyl)-6-methyl-4-(phenylmethyl)-2(1H)-pyridinoneHCID 682953131-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 71543568N-((4-benzyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Procedure

The title compound was prepared in the same manner as described for example 11 from 1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.060 g, 0.292 mmol) and 3(aminomethyl)-6-methyl-4-(phenylmethyl)-2(1H)-pyridinone (0.081 g, 0.307 mmol) wherein the product obtained was further purified by reverse phase HPLC (Gradient B: 5-85%. A:Dichloromethane. B: 10% (2M Ammonia in Methanol) in Chloroform). The isolated product was concentrated from MTBE (2×) to afford a white solid (93 mg, 75%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50 (d, J=6.57 Hz, 6 H), 2.10 (s, 3 H), 3.98 (s, 2 H), 4.45 (d, J=5.05 Hz, 2 H), 5.24 (quin, J=6.63 Hz, 1 H), 5.81 (s, 1 H), 7.12-7.30 (m, 5 H), 7.50 (d, J=4.55 Hz, 1 H), 8.33 (s, 1 H), 8.61 (d, J=4.55 Hz, 1 H), 8.88 (t, J=5.05 Hz, 1 H), 11.63 (s, 1 H). LCMS(ES) [M+H]+ 416.0

Workup

  1. customobtained
  2. customwas further purified by reverse phase HPLC (Gradient B
  3. concentrationThe isolated product was concentrated from MTBE (2×)

Sources & evidence

ORD record
ord-7921311bef0d4e1d8ee03acdb114bb9b
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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