Triethylamine → (E)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-[6-(3-methylureido)pyridin-3-yl]acrylamide

HRID 1921059Notes

Reaction equation

HRID 1921059 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[NH2:5][C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([N:16]([CH3:28])[CH2:17][C:18]2[N:19]([CH3:27])[C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:15])=[CH:8][CH:7]=1.C(N(CC)CC)C>CN(C=O)C>[CH3:28][N:16]([CH2:17][C:18]1[N:19]([CH3:27])[C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14](=[O:15])/[CH:13]=[CH:12]/[C:9]1[CH:10]=[N:11][C:6]([NH:5][C:3]([NH:2][CH3:1])=[O:4])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 52877203-(6-Aminopyridin-3-Yl)-N-Methyl-N-((1-Methyl-1h-Indol-2-Yl)Methyl)Acrylamide

Product 1

HCID 9842686(E)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-[6-(3-methylureido)pyridin-3-yl]acrylamideYield 43.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl isocyanate (0.18 mL, 3.05 mmole) was added to a solution of (E)-3-(6-aminopyridin-3-yl)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide (0.20 g, 0.61 mmole) and triethylamine (0.17 mL, 1.22 mmole) in DMF (20 mL) at RT. The reaction was stirred for 5 days, then was concentrated in vacuo, and the residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated. Flash chromatography on silica gel (ethyl acetate) gave the title compound (0.10 g, 43%) as an off white solid: MS (ES) m/e 378 (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
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-77d9e24136494526aaf7178bf0d204d0
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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