2-(Piperazin-1-yl)pyridine-5-boronic acid, pinacol ester → HCID 54596299, compound

HRID 85486

Reaction equation

HRID 85486 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:15]([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[C:6]([CH3:14])=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.CC1(C)C(C)(C)OB([C:38]2[CH:39]=[CH:40][C:41]([N:44]3[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]3)=[N:42][CH:43]=2)O1>>[CH3:14][C:6]1[C:5]2[C:4]([C:15]([NH:17][CH2:18][C:19]3[C:20](=[O:29])[NH:21][C:22]([CH3:28])=[CH:23][C:24]=3[CH2:25][CH2:26][CH3:27])=[O:16])=[CH:3][C:2]([C:38]3[CH:43]=[N:42][C:41]([N:44]4[CH2:45][CH2:46][NH:47][CH2:48][CH2:49]4)=[CH:40][CH:39]=3)=[CH:10][C:9]=2[N:8]([CH:11]([CH3:13])[CH3:12])[N:7]=1

Participants

3

Reactant 2

HCID 162179462-(Piperazin-1-yl)pyridine-5-boronic acid, pinacol esterHCID 545962236-bromo-1-isopropyl-3-methyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide

Product 1

HCID 54596299HCID 54596299, compound

Procedure

The title compound was prepared in a similar manner as described for example 8 from 6-bromo-3-methyl-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide (65 mg, 0.141 mmol) and 1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]piperazine (61 mg, 0.212 mmol). The product was collected as a white solid (54 mg, 49%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (br. s., 1H) 8.49-8.63 (m, 2H) 8.43 (br. s., 1H) 7.97 (dd, J=8.84, 2.53 Hz, 1H) 7.89 (s, 1H) 7.32 (s, 1H) 6.87-6.96 (m, 1H) 5.91 (s, 1H) 5.03 (dt, J=13.07, 6.47 Hz, 1H) 4.38 (d, J=4.55 Hz, 2H) 3.40-3.61 (m, 5H) 2.77-2.82 (m, 3H) 2.53-2.57 (m, 2H) 2.43 (s, 3H) 2.13 (s, 3H) 1.53-1.60 (m, 2H) 1.46 (s, 3H) 1.44 (s, 3H) 0.93 (t, J=7.33 Hz, 3H); LC-MS (ES) m/z=542.2 [M+H]+

Workup

  1. customThe product was collected as a white solid (54 mg, 49%)

Sources & evidence

ORD record
ord-40527c75f8654a59b855f95aa093608a
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Linked notes

Loading…