3-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetate → 6-bromo-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-1-propyl-1H-indazole-4-carboxamide

HRID 1476423Notes

Reaction equation

HRID 1476423 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]([CH2:11][CH2:12][CH3:13])[C:9]=2[CH:10]=1.[NH2:17][CH2:18][C:19]1[C:20](=[O:29])[NH:21][C:22]([CH3:28])=[CH:23][C:24]=1[CH2:25][CH2:26][CH3:27]>>[Br:1][C:2]1[CH:3]=[C:4]([C:14]([NH:17][CH2:18][C:19]2[C:20](=[O:29])[NH:21][C:22]([CH3:28])=[CH:23][C:24]=2[CH2:25][CH2:26][CH3:27])=[O:16])[C:5]2[CH:6]=[N:7][N:8]([CH2:11][CH2:12][CH3:13])[C:9]=2[CH:10]=1

Participants

3

Reactant 2

HCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetateHCID 674651516-bromo-1-propyl-1H-indazole-4-carboxylic acid

Product 1

HCID 545970736-bromo-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-1-propyl-1H-indazole-4-carboxamideYield 42.5%

Procedure

The title compound was prepared in the same manner as described for example 42 (step b, part 2) from 6-bromo-1-propyl-1H-indazole-4-carboxylic acid (300 mg, 1.06 mmol) and 3-aminomethyl-6-methyl-4-propyl-1H-pyridin-2-one (190 mg, 1.06 mmol). The crude product was triturated with diethyl ether (10 mL) and n-pentane (10 mL) to afford the title compound as a white solid (200 mg, 42.5%). 1H NMR (400 MHz, DMSO-d6): δ 0.88 (t, 3H), 0.90 (t, 3H), 1.48-1.46 (t, 2H), 1.86-1.80 (m, 2H), 2.13 (s, 3H), 2.50-2.32 (t, 2H), 4.40-4.35 (m, 4H), 5.90 (s, 1H), 7.69 (s, 1H), 8.20 (s, 1H), 8.35 (s, 1H), 8.62 (s, 1H), 11.52 (s, 1H). LCMS (ES+): m/z=445.17.

Workup

  1. customThe title compound was prepared in the same manner
  2. customThe crude product was triturated with diethyl ether (10 mL) and n-pentane (10 mL)

Sources & evidence

ORD record
ord-1b9ef4ef2c8a4424ad0f63151896e113
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Reaction notes

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