1,2-Dichloroethane → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-methyl-3-(1-methylethyl)-5-(methyloxy)-1H-indole-7-carboxamide

HRID 1616816Notes

Reaction equation

HRID 1616816 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:14][CH3:15])=[CH:8][C:9]=2[C:11]([OH:13])=O)[C:4]([CH:16]([CH3:18])[CH3:17])=[CH:3]1.Cl.[NH2:20][CH2:21][C:22]1[C:23](=[O:30])[NH:24][C:25]([CH3:29])=[CH:26][C:27]=1[CH3:28].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>CN(C=O)C.C(Cl)Cl.CO>[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:11]([C:9]1[CH:8]=[C:7]([O:14][CH3:15])[CH:6]=[C:5]2[C:10]=1[N:2]([CH3:1])[CH:3]=[C:4]2[CH:16]([CH3:18])[CH3:17])=[O:13]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 438104513-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one hydrochlorideHCID 678142071-Methyl-3-(1-methylethyl)-5-(methyloxy)-1H-indole-7-carboxylic acid

Product 1

HCID 67814426N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-methyl-3-(1-methylethyl)-5-(methyloxy)-1H-indole-7-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent2×

Procedure

To a stirred suspension of 1-methyl-3-(1-methylethyl)-5-(methyloxy)-1H-indole-7-carboxylic acid (78 mg, 0.315 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone hydrochloride (59.5 mg, 0.315 mmol), HOAt (64 mg, 0.473 mmol) in DMF (4 mL) was added EDC (121 mg, 0.631 mmol) and N-methylmorpholine (52 μL, 0.473 mmol). The reaction mixture was stirred for 18 hr at room temperature, after which time the contents were evaporated to near dryness. Water (˜5 mL) was added and the solids which precipitated out were isolated. The collected solid was dissolved in DCM/MeOH (4:1, 5 mL), dried over MgSO4, filtered, and concentrated in vacuo to a afford a creme colored solid. The solid was re-dissolved in DCM/MeOH (4:1, 5 mL) and washed with 6N NaOH (1 mL) and water (4 mL). The organic layer was concentrated in vacuo to afford a nearly white solid.

Workup

  1. customafter which time the contents were evaporated
  2. additionWater (˜5 mL) was added
  3. customthe solids which precipitated out
  4. customwere isolated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to
  8. customa afford a creme colored solid
  9. washwashed with 6N NaOH (1 mL) and water (4 mL)
  10. concentrationThe organic layer was concentrated in vacuo
  11. customto afford a nearly white solid

Sources & evidence

ORD record
ord-54d23bf24dc042c8b5b69c930ac2e61e
Source dataset
uspto-grants-2014_07
Patent number
US08765792B2

Reaction notes

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