Dicyclohexylcarbodiimide → (E)-3-(6-aminopyridin-3-yl)-N-methyl-N-(3-methylbenzo[b]thiophen-2-ylmethyl)acrylamide

HRID 1761130Notes

Reaction equation

HRID 1761130 reaction equation
[CH3:1][C:2]1[C:3]2[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[CH2:7][NH:8][CH3:9].[NH2:14][C:15]1[N:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([OH:25])=O)=[CH:17][CH:16]=1.C1C=CC2N(O)N=NC=2C=1.O.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.C(Cl)Cl>[NH2:14][C:15]1[N:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([N:8]([CH3:9])[CH2:7][C:6]2[S:5][C:4]3[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=3[C:2]=2[CH3:1])=[O:25])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidHCID 22593745N-methyl(3-methylbenzo[b]thiophen-2-yl)methanamine

Product 1

HCID 22593722(E)-3-(6-aminopyridin-3-yl)-N-methyl-N-(3-methylbenzo[b]thiophen-2-ylmethyl)acrylamideYield 72.2%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a stirred solution of 3-methyl-2-(methylaminomethyl)benzo[b]thiophene (0.30 g, 1.6 mmole) in 1:1 DMF/CH2Cl2 was added (E)-3-(6aminopyridin-3-yl)acrylic acid (0.33 g, 2 mmole), HOBt H2O (0.27 g, 2 mmole), and DCC (0.41 g, 2 mmole). The reaction was stirred for 16 hr, then was concentrated under vacuum. The residue was taken up in CHCl3, washed with H2O, dried (Na2SO4) and concentrated. Purification by flash chromatography on silica gel (4% methanoUCHCl3) gave the title compound (0.39 g, 72%) as a pale yellow solid: LCMS (ES) m/e 338.2 (M+H)+.

Workup

  1. concentrationwas concentrated under vacuum
  2. washwashed with H2O
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by flash chromatography on silica gel (4% methanoUCHCl3)

Sources & evidence

ORD record
ord-52e88f842ae244289396c437baa9678a
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

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