1,2-Dichloroethane → 6-bromo-N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide

HRID 1476382Notes

Reaction equation

HRID 1476382 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=O)[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[NH2:17][CH2:18][C:19]1[C:20](=[O:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=1[CH3:25].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([C:14]([NH:17][CH2:18][C:19]2[C:20](=[O:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=2[CH3:25])=[O:16])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:12])[CH3:13])[C:9]=2[CH:10]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 674654436-Bromo-1-isopropyl-1H-indazole-4-carboxylic acid

Product 1

HCID 545964906-bromo-N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamideYield 87.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a mixture of 6-bromo-1-(1-methylethyl)-1H-indazole-4-carboxylic acid (0.52 g, 1.837 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (0.485 g, 2.57 mmol), 1-hydroxy-7-azabenzotriazole (0.375 g, 2.76 mmol) and EDC (0.528 g, 2.76 mmol) in dimethyl sulfoxide (15 mL) was added N-methylmorpholine (0.606 mL, 5.51 mmol) via syringe. The reaction was stirred at RT for 48 h. The contents were slowly diluted into 200 mL of water, stirred for 10 min, then allowed to sit for 20 min. The suspension was filtered. The collected solid was washed with about 50 mL of water, filtered, air dried for 15 min then dried in vac oven to afford the title compound (0.67 g, 85%), which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45 (d, J=6.57 Hz, 6H) 2.12 (s, 3H) 2.20 (s, 3H) 4.33 (d, J=5.05 Hz, 2H) 5.05 (quin, J=6.57 Hz, 1H) 5.89 (s, 1H) 7.71 (d, J=1.26 Hz, 1H) 8.20 (s, 1H) 8.37 (s, 1H) 8.62 (t, J=4.67 Hz, 1H) 11.54 (s, 1H). MS (ES) [M+H]+ 417.1.

Workup

  1. stirringstirred for 10 min
  2. waitto sit for 20 min
  3. filtrationThe suspension was filtered
  4. washThe collected solid was washed with about 50 mL of water
  5. filtrationfiltered
  6. customair dried for 15 min
  7. customthen dried in vac oven

Sources & evidence

ORD record
ord-410984c3c7a6425988f770541ed3ed3f
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Reaction notes

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