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

HRID 225940Notes

Reaction equation

HRID 225940 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

7

Reactant 5

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 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-(6-aminopyridin-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% methanol/CHCl3) gave the title compound (0.39 g, 72%) as a pale yellow solid: LCMS (ES) m/e 338.2 (M+H)+.

Workup

  1. concentrationthen was concentrated under vacuum
  2. washwashed with H2O
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by flash chromatography on silica gel (4% methanol/CHCl3)

Sources & evidence

ORD record
ord-4f1d8da1974b4fa2a027f30e9d0ba855
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

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