3-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one → N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-3-methyl-6-(1H-pyrazol-4-yl)-1H-indazole-4-carboxamide

HRID 85501Notes

Reaction equation

HRID 85501 reaction equation
[CH:1]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]3[CH:14]=[N:15][NH:16][CH:17]=3)[CH:9]=[C:8]([C:18]([OH:20])=O)[C:7]=2[C:6]([CH3:21])=[N:5]1)([CH3:3])[CH3:2].[NH2:22][CH2:23][C:24]1[C:25](=[O:32])[NH:26][C:27]([CH3:31])=[CH:28][C:29]=1[CH3:30]>>[CH3:30][C:29]1[CH:28]=[C:27]([CH3:31])[NH:26][C:25](=[O:32])[C:24]=1[CH2:23][NH:22][C:18]([C:8]1[C:7]2[C:6]([CH3:21])=[N:5][N:4]([CH:1]([CH3:3])[CH3:2])[C:12]=2[CH:11]=[C:10]([C:13]2[CH:14]=[N:15][NH:16][CH:17]=2)[CH:9]=1)=[O:20]

Participants

3

Reactant 2

HCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 67465229HCID 67465229, compound

Product 1

HCID 54596429N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-3-methyl-6-(1H-pyrazol-4-yl)-1H-indazole-4-carboxamide

Procedure

The title compound was prepared from 1-isopropyl-3-methyl-6-(1H-pyrazol-4-yl)-1H-indazole-4-carboxylic acid and 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one (0.059 g, 0.387 mmol) in the same manner as described for example 80 (step c) wherein the contents were stirred at RT for 5 h. The product was collected as a pale yellow solid (30 mg, 20%). 1H NMR (DMSO-d6, 400 MHz): 1.563 (d, J=6.8 Hz, 6H), 2.207 (s, 3H), 2.455 (s, 3H), 2.556 (s, 3H), 4.616 (d, J=6 Hz, 2H), 4.781-4.798 (m, 1H), 5.899 (s, 1H), 7.236 (s, 1H), 7.488 (s, 1H) 7.522 (s, 1H), 7.797 (d, J=9.6 Hz, 2H). LCMS (ES+) m/z: 419.45.

Workup

  1. customThe product was collected as a pale yellow solid (30 mg, 20%)

Sources & evidence

ORD record
ord-fa229f06a82c4d15a0c2a6cf4b23ad2e
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Reaction notes

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