3-(aminomethyl)-6-methyl-4-(phenylmethyl)-2(1H)-pyridinone → 6-bromo-1-(1-methylethyl)-N-{[6-methyl-2-oxo-4-(phenylmethyl)-1,2-dihydro-3-pyridinyl]methyl}-1H-indazole-4-carboxamide

HRID 1476384Notes

Reaction equation

HRID 1476384 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:33])[NH:21][C:22]([CH3:32])=[CH:23][C:24]=1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[Br:1][C:2]1[CH:3]=[C:4]([C:14]([NH:17][CH2:18][C:19]2[C:20](=[O:33])[NH:21][C:22]([CH3:32])=[CH:23][C:24]=2[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[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 674636783-(aminomethyl)-6-methyl-4-(phenylmethyl)-2(1H)-pyridinoneHCID 674654436-Bromo-1-isopropyl-1H-indazole-4-carboxylic acid

Product 1

HCID 545965546-bromo-1-(1-methylethyl)-N-{[6-methyl-2-oxo-4-(phenylmethyl)-1,2-dihydro-3-pyridinyl]methyl}-1H-indazole-4-carboxamide

Procedure

The title compound was prepared in the same manner as described for the example 4 from 6-bromo-1-(1-methylethyl)-1H-indazole-4-carboxylic acid (100 mg, 0.353 mmol) and 3-(aminomethyl)-6-methyl-4-(phenylmethyl)-2(1H)-pyridinone (129 mg, 0.565 mmol), wherein the reaction stir time was 12 h. The product was collected as a white solid (130 mg, 71%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.61 (s, 1H), 8.69 (s, 1H), 8.35 (s, 1H), 8.20 (s, 1H), 7.66 (s, 1H), 7.17-7.26 (m, 6H), 5.81 (s, 1H), 5.04 (m, 2H), 4.42 (s, 2H), 3.96 (s, 2H), 2.10 (s, 3H), 1.45 (d, 6H); MS (ES) [M+H]+ 495.0.

Workup

  1. customThe product was collected as a white solid (130 mg, 71%)

Sources & evidence

ORD record
ord-507728dfa98a4faf80890454e1581383
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Reaction notes

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