1,4-Dioxane → 6-{3-[(dimethylamino)methyl]phenyl}-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide hydrochloride salt

HRID 1476409Notes

Reaction equation

HRID 1476409 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.[ClH:29].[CH3:30][N:31]([CH2:33][C:34]1[CH:35]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH:37]=[CH:38][CH:39]=1)[CH3:32].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O>[ClH:29].[CH3:30][N:31]([CH2:33][C:34]1[CH:39]=[C:38]([C:2]2[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]3[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=3[CH:10]=2)[CH:37]=[CH:36][CH:35]=1)[CH3:32]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 44118822N,N-Dimethyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine hydrochlorideHCID 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 545969196-{3-[(dimethylamino)methyl]phenyl}-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide hydrochloride salt

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolvent

Procedure

The title compound was prepared in the same manner as described for example 33 using from 6-bromo-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide (200 mg, 0.449 mmol), 3-(N,N dimethylaminomethyl)phenylboronic acid pinacol ester hydrochloride (170 mg, 0.571 mmol), potassium phosphate (300 mg, 1.413 mmol), dioxane (12 mL), water (3 mL), and PdCl2(dppf)-CH2Cl2 adduct (50 mg, 0.061 mmol). The product was obtained as a light tan solid (204 mg, 85% yield). 1H NMR (400 MHz, DMSO-d6) δ=11.67 (br. s., 1H), 10.97 (br. s., 1H), 8.68 (t, J=5.1 Hz, 1H), 8.38 (s, 1H), 8.30 (s, 1H), 8.16 (s, 1H), 8.00-7.94 (m, 1H), 7.92 (d, J=1.0 Hz, 1H), 7.65-7.53 (m, 2H), 5.96 (s, 1H), 5.18 (dt, J=6.6, 13.3 Hz, 1H), 4.43 (d, J=5.1 Hz, 2H), 4.38 (d, J=5.6 Hz, 2H), 2.74 (d, J=4.8 Hz, 6H), 2.61-2.52 (m, 2H), 2.15 (s, 3H), 1.59-1.52 (m, 2H), 1.51 (d, J=6.6 Hz, 6H), 0.90 (t, J=7.3 Hz, 3H); LC-MS (ES)+ m/e 500.2 [M+H]+.

Sources & evidence

ORD record
ord-cb69af95ee0042ea8125e2a05817d7c6
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Reaction notes

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