1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-(1-methyl-1H-pyrazol-4-yl)-1H-indazole-4-carboxamide

HRID 85464Notes

Reaction equation

HRID 85464 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:16]([NH:18][CH2:19][C:20]2[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=2[CH3:26])=[O:17])[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.[CH3:29][N:30]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[N:31]1>>[CH:11]1([N:8]2[C:9]3[CH:10]=[C:2]([C:33]4[CH:32]=[N:31][N:30]([CH3:29])[CH:34]=4)[CH:3]=[C:4]([C:16]([NH:18][CH2:19][C:20]4[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=4[CH3:26])=[O:17])[C:5]=3[CH:6]=[N:7]2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 545970746-bromo-1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-1H-indazole-4-carboxamide

Product 1

HCID 545972271-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-(1-methyl-1H-pyrazol-4-yl)-1H-indazole-4-carboxamide

Procedure

The title compound was prepared in a similar manner as described for example 8 from 6-bromo-1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide (100 mg, 0.226 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (70 mg, 0.338 mmol). The product was collected as a white solid (82 mg, 81%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.53 (br. s., 1H) 8.48 (t, J=4.93 Hz, 1H) 8.30 (s, 1H) 8.26 (s, 1H) 8.04 (s, 2H) 7.81 (s, 1H) 5.90 (s, 1H) 5.22 (quin, J=7.14 Hz, 1H) 4.39 (s, 1H) 4.38 (s, 1H) 3.87-3.92 (m, 3H) 2.23 (s, 3H) 2.14-2.19 (m, 1H) 2.13 (s, 4H) 1.96-2.05 (m, 2H) 1.84-1.94 (m, 2H) 1.66-1.76 (m, 2H). LC-MS (ES) m/z=445.2 [M+H]+

Workup

  1. customThe product was collected as a white solid (82 mg, 81%)

Sources & evidence

ORD record
ord-83c84453fb4e406398fea6611d8688b0
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Reaction notes

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