1,2-Dichloroethane → HCID 9818527, compound

HRID 225928Notes

Reaction equation

HRID 225928 reaction equation
C(Cl)CCl.[C:5]([OH:9])(=O)[CH:6]=[CH2:7].[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][NH:21][CH3:22])=[CH:12]1.[CH:23]1[CH:24]=[CH:25][C:26]2N(O)N=[N:29][C:27]=2C=1.O.C([N:37](C(C)C)CC)(C)C>CN(C=O)C>[NH2:37][C:27]1[N:29]=[CH:23][C:24](/[CH:7]=[CH:6]/[C:5]([N:21]([CH3:22])[CH2:20][C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]([CH3:10])[CH:12]=2)=[O:9])=[CH:25][CH:26]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 6581Acrylic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 109867781-Methyl-3-(methylaminomethyl)indole

Product 1

HCID 9818527HCID 9818527, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (035 g, 1.89 mmole) was added to a solution of 3-6-aminopyridin-3-yl)acrylic acid (0.31 g, 1.89 mmole), 1-methyl-3-(methylaminomethyl)-1H-indole (0.30 g, 1.72 mmole), HOBt.H2O (0.24 g, 1.89 mmole) and diisopropylethylamine (0.60 mL, 3.44 mmole) in DMF (20 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 (0.30 g, 55%) as a light yellow solid: MS (ES) m/e 321 (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-ec72e9b00b784c679b630876fe9bd520
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

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