1,2-Dichloroethane → N-((4,6-Dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(trifluoromethyl)-1H-indole-4-carboxamide

HRID 42419Notes

Reaction equation

HRID 42419 reaction equation
[CH3:1][CH:2]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=[C:8]([C:17](O)=[O:18])[C:7]=2[CH:6]=[CH:5]1)[CH3:3].[NH2:20][CH2:21][C:22]1[C:23](=[O:30])[NH:24][C:25]([CH3:29])=[CH:26][C:27]=1[CH3:28].CN1CCOCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CS(C)=O>[CH3:28][C:27]1[CH:26]=[C:25]([CH3:29])[NH:24][C:23](=[O:30])[C:22]=1[CH2:21][NH:20][C:17]([C:8]1[C:7]2[CH:6]=[CH:5][N:4]([CH:2]([CH3:3])[CH3:1])[C:12]=2[CH:11]=[C:10]([C:13]([F:15])([F:16])[F:14])[CH:9]=1)=[O:18]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 674642241-Isopropyl-6-(trifluoromethyl)-1H-indole-4-carboxylic acid

Product 1

HCID 67468150N-((4,6-Dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(trifluoromethyl)-1H-indole-4-carboxamideYield 65.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-(1-methylethyl)-6-(trifluoromethyl)-1H-indole-4-carboxylic acid (40 mg, 0.147 mmol) in dimethyl sulfoxide (1 mL) were added 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (41.7 mg, 0.221 mmol), N-methylmorpholine (0.065 mL, 0.590 mmol), 1-hydroxy-7-azabenzotriazole (40.1 mg, 0.295 mmol) and EDC (56.5 mg, 0.295 mmol), and the mixture was stirred overnight. The mixture was quenched with water (5 mL) and stirred for 10 min. The precipitate was collected by filtration and dried under high vacuum to give the title compound (39 mg, 63%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.47 (m, 6H), 2.13 (s, 3H), 2.23 (s, 3H), 4.36 (d, J=5.05 Hz, 2H), 4.99 (dt, J=13.20, 6.66 Hz, 1H), 5.89 (s, 1H), 6.98 (d, J=3.03 Hz, 1H), 7.68 (s, 1H), 7.86 (d, J=3.28 Hz, 1H), 8.08 (s, 1H), 8.45 (t, J=4.93 Hz, 1H), 11.56 (s, 1H). MS: (M+H)+=406.1.

Workup

  1. customThe mixture was quenched with water (5 mL)
  2. stirringstirred for 10 min
  3. filtrationThe precipitate was collected by filtration
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-fb05e77f63a745fc9025562809c76ba3
Source dataset
uspto-grants-2013_09
Patent number
US08536179B2

Reaction notes

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