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

HRID 85468Notes

Reaction equation

HRID 85468 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:16]([OH:18])=O)[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:9]=2[CH:10]=1.[NH2:19][CH2:20][C:21]1[C:22](=[O:31])[NH:23][C:24]([CH3:30])=[CH:25][C:26]=1[CH2:27][CH2:28][CH3:29]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:16]([NH:19][CH2:20][C:21]2[C:22](=[O:31])[NH:23][C:24]([CH3:30])=[CH:25][C:26]=2[CH2:27][CH2:28][CH3:29])=[O:18])[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[C:9]=2[CH:10]=1

Participants

3

Reactant 2

HCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetateHCID 674667106-chloro-1-cyclopentyl-1H-indazole-4-carboxylic acid

Product 1

HCID 545972986-chloro-1-cyclopentyl-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-chloro-1-cyclopentyl-1H-indazole-4-carboxylic acid (0.12 g, 0.453 mmol) and 3-(aminomethyl)-6-methyl-4-propyl-2(1H)-pyridinone (0.128 g, 0.680 mmol). The final product was collected as 0.170 g (86%); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.89 (t, J=7.33 Hz, 3H), 1.45-1.57 (m, 2H), 1.61-1.74 (m, 2H), 1.80-1.92 (m, 2H), 1.92-2.03 (m, 2H), 2.05-2.19 (m, 5H), 4.36 (d, J=5.05 Hz, 2H), 5.21 (t, J=7.07 Hz, 1H), 5.91 (s, 1H), 7.59 (d, J=1.52 Hz, 1H), 8.06 (s, 1H), 8.37 (s, 1H), 8.62 (t, J=4.80 Hz, 1H), 11.55 (s, 1H); LC-MS (ES) m/z=426.7 [M+H]+

Workup

  1. customThe final product was collected as 0.170 g (86%)

Sources & evidence

ORD record
ord-af5db42f8dc243ecb93af62af9aabdf4
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Reaction notes

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