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

HRID 1761120Notes

Reaction equation

HRID 1761120 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[CH3:13][NH:14][CH2:15][C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2.C1C=CC2N(O)N=NC=2C=1.O.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(Cl)CCl>[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:14]([CH2:15][C:16]2[NH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:13])=[O:12])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 11194490N-Methyl-1H-indole-2-methanamineHCID 534008323-(6-Aminopyridin-3-yl)prop-2-enoic acid

Product 1

HCID 9861351(E)-3-(6-aminopyridin-3-yl)-N-(1H-indol-2-ylmethyl)-N-methylacrylamideYield 68.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

EDC (0.30 g, 1.5B mmole) was added to a solution of 3-(6aminopyridin-3-yl)acrylic acid (0.26 g. 1.58 mmole), 2-(methylaminomethyl)-1H-indole (0.23 g, 1.43 mmole), HOBt H2O (0.21 g, 1.58 mmole) and diisopropylethylamine (0.51 mL, 2.86 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 (10% MeOHICHCl3) gave the title compound (0.30 g, 68%) as a light yellow solid: MS (ES) m/e 307 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-68d3c42fe120454093305452fbc5b8d9
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

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