1,2-Dichloroethane → (E)-3-(6-aminopyridin-3-yl)-N-(1-ethyl-1H-indol-2-ylmethyl)-N-methylacrylamide

HRID 225927Notes

Reaction equation

HRID 225927 reaction equation
C(Cl)CCl.[NH2:5][C:6]1[N:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]([OH:16])=O)=[CH:8][CH:7]=1.[CH2:17]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[C:20]1[CH2:28][NH:29][CH3:30])[CH3:18].C1C=CC2N(O)N=NC=2C=1.O.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH2:5][C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([N:29]([CH2:28][C:20]2[N:19]([CH2:17][CH3:18])[C:27]3[C:22]([CH:21]=2)=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH3:30])=[O:16])=[CH:8][CH:7]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 225937291-Ethyl-2-(methylaminomethyl)-1H-indoleHCID 534008323-(6-Aminopyridin-3-yl)prop-2-enoic acid

Product 1

HCID 57440849(E)-3-(6-aminopyridin-3-yl)-N-(1-ethyl-1H-indol-2-ylmethyl)-N-methylacrylamideYield 30.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (0.84 g, 4.38 mmole) was added to a solution of 3-(6-aminopyridin-3-yl)acrylic acid (0.72 g, 4.38 mmole), 1-ethyl-2-(methylaminomethyl)-1H-indole (0.75 g, 3.98 mmole), HOBt.H2O (0.59 g, 4.38 mmole) and diisopropylethylamine (1.40 mL, 7.96 mmole) in DMF (30 mL) at RT. The reaction was stirred overnight, then was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4. Flash chromatography on silica gel (5% MeOH/CHCl3) gave the title compound (0.40 g, 30%) as a light tan solid: MS (ES) m/e 335 (M+H)+.

Workup

  1. customat RT
  2. concentrationwas concentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-b309c0c1817e48c3adaa4ee7e8f70eca
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

Loading…