1,2-Dichloroethane → 6-(4-(dimethylamino)piperidin-1-yl)-1-isopropyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide

HRID 85449Notes

Reaction equation

HRID 85449 reaction equation
[CH3:1][N:2]([CH3:24])[CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[C:11]([C:21](O)=[O:22])[C:12]3[CH:13]=[N:14][N:15]([CH:18]([CH3:20])[CH3:19])[C:16]=3[CH:17]=2)[CH2:5][CH2:4]1.[NH2:25][CH2:26][C:27]1[C:28](=[O:37])[NH:29][C:30]([CH3:36])=[CH:31][C:32]=1[CH2:33][CH2:34][CH3:35].CN1CCOCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CS(C)=O>[CH3:24][N:2]([CH3:1])[CH:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:10]=[C:11]([C:21]([NH:25][CH2:26][C:27]3[C:28](=[O:37])[NH:29][C:30]([CH3:36])=[CH:31][C:32]=3[CH2:33][CH2:34][CH3:35])=[O:22])[C:12]3[CH:13]=[N:14][N:15]([CH:18]([CH3:19])[CH3:20])[C:16]=3[CH:17]=2)[CH2:7][CH2:8]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetateHCID 674652136-[4-(dimethylamino)-1-piperidinyl]-1-(1-methylethyl)-1H-indazole-4-carboxylic acid

Product 1

HCID 545969966-(4-(dimethylamino)piperidin-1-yl)-1-isopropyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamideYield 67%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-[4-(dimethylamino)-1-piperidinyl]-1-(1-methylethyl)-1H-indazole-4-carboxylic acid (34 mg, 0.103 mmol) in DMSO (1 mL) were added 3-(aminomethyl)-6-methyl-4-propyl-2(1H)-pyridinone (29.0 mg, 0.134 mmol), N-methylmorpholine (0.045 mL, 0.412 mmol), 1-hydroxy-7-azabenzotriazole (28.0 mg, 0.206 mmol) and EDC (39.5 mg, 0.206 mmol), and the mixture was stirred for 48 h. The mixture was purified using reverse-phase HPLC to afford the title compound as a pale yellow solid (34 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.77-0.96 (m, 3H), 1.43 (d, J=6.57 Hz, 6H), 1.46-1.66 (m, 4H), 1.89 (m, 2H), 2.13 (s, 3H), 2.31 (s, 6H), 2.33 (m, 2H), 2.55 (s, 3H), 2.65-2.84 (m, 2H), 3.86 (m, 2H), 4.38 (m, 2H), 4.85-5.04 (m, 1H), 5.91 (s, 1H), 7.07 (s, 1H), 7.32 (m, 1H), 8.15 (m, 1H), 8.25 (br. s., 1H), 8.44 (t, J=4.93 Hz, 1H); LCMS: (M+H)+=493.2

Workup

  1. customThe mixture was purified

Sources & evidence

ORD record
ord-5b555e81b79740cba76d2de390e1ecb4
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Reaction notes

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