3-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one → 6-bromo-1-cyclopropyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide

HRID 1476440Notes

Reaction equation

HRID 1476440 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:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=1[CH3:25]>>[Br:1][C:2]1[CH:3]=[C:4]([C:14]([NH:17][CH2:18][C:19]2[C:20](=[O:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=2[CH3:25])=[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 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 674646356-bromo-1-cyclopropyl-1H-indazole-4-carboxylic acid

Product 1

HCID 545962186-bromo-1-cyclopropyl-N-[(4,6-dimethyl-2-oxo-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)-4,6-dimethyl-2(1H)-pyridinone (0.221 g, 1.174 mmol), wherein the reaction stir time was 12 h. The title compound was collected as a white solid (0.27 g, 81%); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.06-1.17 (m, 4H), 2.12 (s, 3H), 2.20 (s, 3H), 3.76-3.85 (m, 1H), 4.33 (d, J=5.05 Hz, 2H), 5.88 (s, 1H), 7.76 (d, J=1.52 Hz, 1H), 8.10 (s, 1H), 8.30 (d, J=1.01 Hz, 1H), 8.64 (t, J=4.93 Hz, 1H), 11.54 (s, 1H); LC-MS (ES) m/z=414.8 [M+H].

Workup

  1. customThe title compound was collected as a white solid (0.27 g, 81%)

Sources & evidence

ORD record
ord-ff7a1b6b818348f49b24eb23067ff563
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Reaction notes

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