3-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetate → 6-bromo-1-cyclopropyl-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide

HRID 85475Notes

Reaction equation

HRID 85475 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]3[CH2:13][CH2:12]3)[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]([CH:11]3[CH2:12][CH2:13]3)[C:9]=2[CH:10]=1

Participants

3

Reactant 2

HCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetateHCID 67464635HCID 67464635, compound

Product 1

HCID 545962196-bromo-1-cyclopropyl-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-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-cyclopropyl-1H-indazole-4-carboxylic acid (0.22 g, 0.783 mmol) and 3-(aminomethyl)-6-methyl-4-propyl-2(1H)-pyridinone (0.236 g, 1.089 mmol), wherein the reaction stir time was 12 h. The title compound was collected as a white solid (0.36 g, 91%); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.88 (t, J=7.33 Hz, 3H), 1.06-1.16 (m, 4H), 1.50 (sxt, J=7.53 Hz, 2H), 2.13 (s, 3H), 3.76-3.86 (m, 1H), 4.36 (d, J=5.05 Hz, 2H), 5.90 (s, 1H), 7.74 (d, J=1.52 Hz, 1H), 8.09 (s, 1H), 8.31 (s, 1H), 8.64 (t, J=4.80 Hz, 1H), 11.54 (br. s., 1H); LC-MS (ES) m/z=443.0 [M+H].

Workup

  1. customThe title compound was collected as a white solid (0.36 g, 91%)

Sources & evidence

ORD record
ord-15634e89e98a45798f33e660448eb897
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Reaction notes

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