3-(N,N-Dimethylaminomethyl)phenylboronic acid, pinacol ester → 6-(3-((dimethylamino)methyl)phenyl)-N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide

HRID 85441Notes

Reaction equation

HRID 85441 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[CH3:27][N:28]([CH3:45])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=1>>[CH3:27][N:28]([CH2:29][C:30]1[CH:31]=[C:32]([C:2]2[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]3[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=3[CH3:24])=[O:15])[C:5]3[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=3[CH:10]=2)[CH:33]=[CH:34][CH:35]=1)[CH3:45]

Participants

3

Reactant 2

HCID 38036203-(N,N-Dimethylaminomethyl)phenylboronic acid, pinacol esterHCID 545964906-bromo-N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide

Product 1

HCID 545968406-(3-((dimethylamino)methyl)phenyl)-N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide

Procedure

The title compound was prepared in a similar manner as described for example 12 from 6-bromo-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-methyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide (100 mg, 0.240 mmol) and dimethyl{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}amine (93 mg, 0.312 mmol). The product obtained from HPLC purification was treated with a saturated solution of NaHCO3, solids that crashed out were filtered, and air-dried for 15 min. The product was then triturated first from EtOAc (containing EtOH) and then hexanes. The solid was then concentrated from MeOH, and triturated with ether, and then dried in vacuum oven overnight. The product was collected as a white solid (56 mg, 56%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.53 (s, 1H) 8.66 (t, J=4.93 Hz, 1H) 8.37 (s, 1H) 8.09 (s, 1H) 7.83 (s, 1H) 7.71-7.76 (m, 2H) 7.46 (t, J=7.96 Hz, 1H) 7.33 (d, J=7.58 Hz, 1H) 5.89 (s, 1H) 5.19 (quin, J=6.63 Hz, 1H) 4.40 (s, 1H) 4.39 (s, 1H) 3.49 (s, 2H) 2.22 (s, 3H) 2.19 (s, 6H) 2.12 (s, 3H) 1.51 (s, 3H) 1.49 (s, 3H); LC-MS (ES) m/z=472.2 [M+H]+

Workup

  1. customThe product obtained from HPLC purification
  2. additionwas treated with a saturated solution of NaHCO3, solids that
  3. filtrationcrashed out were filtered
  4. customair-dried for 15 min
  5. customThe product was then triturated first from EtOAc (containing EtOH)
  6. concentrationThe solid was then concentrated from MeOH
  7. customtriturated with ether
  8. customdried in vacuum oven overnight
  9. customThe product was collected as a white solid (56 mg, 56%)

Sources & evidence

ORD record
ord-99ce56a93e4f4ca99969e10e5b58ee77
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Reaction notes

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