6-Bromo-1-isopropyl-1H-indazole-4-carboxylic acid → 6-bromo-N-((4-(sec-butyl)-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl 1H-indazole-4-carboxamide

HRID 85514Notes

Reaction equation

HRID 85514 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=O)[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[NH2:17][CH2:18][C:19]1[C:20](=[O:30])[NH:21][C:22]([CH3:29])=[CH:23][C:24]=1[CH:25]([CH2:27][CH3:28])[CH3:26]>>[Br:1][C:2]1[CH:3]=[C:4]([C:14]([NH:17][CH2:18][C:19]2[C:20](=[O:30])[NH:21][C:22]([CH3:29])=[CH:23][C:24]=2[CH:25]([CH2:27][CH3:28])[CH3:26])=[O:16])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:12])[CH3:13])[C:9]=2[CH:10]=1

Participants

3

Reactant 2

HCID 674654436-Bromo-1-isopropyl-1H-indazole-4-carboxylic acidHCID 674678593-(aminomethyl)-4-(sec-butyl)-6-methylpyridin-2(1H)-one

Product 1

HCID 545966286-bromo-N-((4-(sec-butyl)-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl 1H-indazole-4-carboxamide

Procedure

The title compound was prepared in the same manner as described for example 3 (step c) from 6-bromo-1-(1-methylethyl)-1H-indazole-4-carboxylic acid (0.50 g, 1.77 mmol) and 3-(aminomethyl)-4-(sec-butyl)-6-methylpyridin-2(1H)-one (0.446 g, 2.296 mmol). The product was collected as 0.81 g (98%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.53 (s, 1H), 8.62 (t, J=4.7 Hz, 1H), 8.37 (s, 1H), 8.20 (s, 1H), 7.70 (d, J=1.5 Hz, 1H), 5.96 (s, 1H), 5.05 (quin, J=6.6 Hz, 1H), 4.41 (d, J=4.3 Hz, 2H), 2.95 (q, J=7.1 Hz, 1H), 2.15 (s, 3H), 1.48 (m, 8H), 1.07 (d, J=6.6 Hz, 3H), 0.74 (t, J=7.3 Hz, 3H). LC-MS(ES) [M+H]+ 459.2.

Workup

  1. customThe product was collected as 0.81 g (98%)

Sources & evidence

ORD record
ord-54dff8cef13e495dbefcff6fe729726f
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Reaction notes

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