1,2-Dichloroethane → HCID 67812886, compound

HRID 1616814Notes

Reaction equation

HRID 1616814 reaction equation
[CH:1]([C:4]1[C:12]2[C:7](=[C:8]([C:17](O)=[O:18])[CH:9]=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=2)[N:6]([CH3:20])[CH:5]=1)([CH3:3])[CH3:2].Cl.[NH2:22][CH2:23][C:24]1[C:25](=[O:32])[NH:26][C:27]([CH3:31])=[CH:28][C:29]=1[CH3:30].ON1C2N=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:30][C:29]1[CH:28]=[C:27]([CH3:31])[NH:26][C:25](=[O:32])[C:24]=1[CH2:23][NH:22][C:17]([C:8]1[CH:9]=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=[C:12]2[C:7]=1[N:6]([CH3:20])[CH:5]=[C:4]2[CH:1]([CH3:2])[CH3:3])=[O:18]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 11430Potassium CarbonateHCID 181649HOAtHCID 438104513-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one hydrochlorideHCID 67814566HCID 67814566, compound

Product 1

HCID 67812886HCID 67812886, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Isopropyl-1-methyl-5-(methylsulfonyl)-1H-indole-7-carboxylic acid (80.7 mg, 0.27 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone hydrochloride (66.2 mg, 0.35 mmol) and 1-hydroxy-7-azabenzotriazole (56.7 mg, 0.42 mmol) were stirred in 3 mL of DMSO for 10 min under nitrogen. N-methylmorpholine (0.12 mL, 1.09 mmol) was added along with EDC (78.3 mg, 0.41 mmol) and the mixture was stirred at room temperature for 19 hours. Ice-water (15 mL) and a concentrated solution of potassium carbonate were added to pH 10 and the solution was stirred for 40 minutes at room temperature. The solids were filtered, washed with water and dried. DMF was added along with water, solids were filtered and dried in vacuum-oven overnight to give N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-isopropyl-1-methyl-5-(methylsulfonyl)-1H-indole-7-carboxamide (88 mg, 73%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.31 (d, J=6.8 Hz, 6H) 2.12 (s, 3H) 2.24 (s, 3H) 3.18-3.26 (m, 4H) 3.71-3.75 (m, 3H) 4.36 (d, J=4.80 Hz, 2H) 5.89 (s, 1H) 7.33 (s, 1H) 7.51 (d, J=1.77 Hz, 1H) 8.14 (d, J=2.02 Hz, 1H) 8.65 (t, J=4.93 Hz, 1H) 11.52 (s, 1H). MS (ES) [M+H]+ 430.3.

Workup

  1. stirringthe solution was stirred for 40 minutes at room temperature
  2. filtrationThe solids were filtered
  3. washwashed with water
  4. customdried
  5. additionDMF was added along with water, solids
  6. filtrationwere filtered
  7. customdried in vacuum-oven overnight

Sources & evidence

ORD record
ord-e3d93071b5904c56acdea99013889273
Source dataset
uspto-grants-2014_07
Patent number
US08765792B2

Reaction notes

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