(Pyrimidin-5-yl)boronic acid → 1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-(5-pyrimidinyl)-1H-indazole-4-carboxamide

HRID 85434Notes

Reaction equation

HRID 85434 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:28])[NH:20][C:21]([CH3:27])=[CH:22][C:23]=2[CH2:24][CH2:25][CH3:26])=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[N:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[N:31][CH:30]=1>>[CH3:12][CH:11]([N:8]1[C:9]2[CH:10]=[C:2]([C:33]3[CH:34]=[N:29][CH:30]=[N:31][CH:32]=3)[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]3[C:19](=[O:28])[NH:20][C:21]([CH3:27])=[CH:22][C:23]=3[CH2:24][CH2:25][CH3:26])=[O:15])[C:5]=2[CH:6]=[N:7]1)[CH3:13]

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 674653266-bromo-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide

Product 1

HCID 545967621-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-(5-pyrimidinyl)-1H-indazole-4-carboxamide

Procedure

The title compound was prepared in the same manner as described for example 75 from 6-bromo-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide (100 mg, 0.225 mmol) and 5-pyrimidinylboronic acid (42 mg, 0.337 mmol). The final product was collected as a white solid (77 mg, 75%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.55 (s, 1H) 9.35 (s, 2H) 9.21-9.26 (m, 1H) 8.63 (t, J=4.93 Hz, 1H) 8.45 (s, 1H) 8.38 (s, 1H) 7.99 (d, J=1.26 Hz, 1H) 5.92 (s, 1H) 5.18 (quin, J=6.57 Hz, 1H) 4.44 (s, 1H) 4.42 (s, 1H) 2.52-2.56 (m, 2H) 2.13 (s, 3H) 1.52-1.56 (m, 4H) 1.48-1.52 (m, 4H) 0.88 (t, J=7.33 Hz, 3H). LC-MS (ES) m/z=445.2

Workup

  1. customThe final product was collected as a white solid (77 mg, 75%)

Sources & evidence

ORD record
ord-21dbbace8c724ee0b51e0cfc9c854e58
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Reaction notes

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