Methylamine → (E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-[6-[N-(methylaminocarbonylmethyl)amino]pyridin-3-yl]acrylamide

HRID 18325Notes

Reaction equation

HRID 18325 reaction equation
C[O:2][C:3]([CH2:5][NH:6][C:7]1[N:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([N:17]([CH3:29])[CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][C:20]=2[CH3:28])=[O:16])=[CH:9][CH:8]=1)=O.[CH3:30][NH2:31]>CO>[CH3:29][N:17]([CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][C:20]=1[CH3:28])[C:15](=[O:16])/[CH:14]=[CH:13]/[C:10]1[CH:11]=[N:12][C:7]([NH:6][CH2:5][C:3]([NH:31][CH3:30])=[O:2])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 10363109(E)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)acrylamide

Product 1

HCID 10045982(E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-[6-[N-(methylaminocarbonylmethyl)amino]pyridin-3-yl]acrylamideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (E)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)acrylamide (0.7 g, 1.8 mmole) was added a solution of 2.0 M methylamine in MeOH (50 mL). After stirring for 72 h the reaction was concentrated to dryness. The residue was triturated with Et2O, filtered, and dried under vacuum to give the title compound (0.703 g, 100%) as an off-white solid: MS (ES) m/e 392.2 (M+H)+.

Workup

  1. concentrationwas concentrated to dryness
  2. customThe residue was triturated with Et2O
  3. filtrationfiltered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b36be5eb2cf94f12937f5d6089d40b57
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Reaction notes

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