1,2-Dichloroethane → HCID 9818411, compound

HRID 2112717Notes

Reaction equation

HRID 2112717 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[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1.C1C=CC2N(O)N=NC=2C=1.O.CCN(CC)CC.C(Cl)CCl>CN(C=O)C.C(Cl)Cl>[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:14]([CH3:13])[CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)=[O:12])=[CH:4][CH:3]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 541935Methyl[(naphthalen-2-yl)methyl]amineHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acid

Product 1

HCID 9818411HCID 9818411, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a stirred solution of (E)-3-(6-aminopyridin-3-yl)acrylic acid (0.30 g, 1.8 mmole) in 1:1 DMF/CH2Cl2 (25 mL) was added 2-(methylaminomethyl)naphthalene (0.34 g, 2 mmole), HOBt.H2O (0.27 g, 2 mmole), Et3N (0.28 mL, 2 mmole), and EDC (0.38 g, 2 mmole). After stirring at RT for 16 hr the reaction was concentrated under vacuum. The residue was taken up in ethyl acetate and the solution was washed with H2O, dried (Na2SO4) and concentrated to dryness. Purification by flash chromatography on silica gel (4% methanol/CHCl3), trituration with 1:1 ethyl acetate/hexane, filtration, and drying under vacuum gave the title compound (0.49 g, 81%) as an off-white solid: LCMS (ES) m/e 318.0 (M+H)+.

Workup

  1. concentrationwas concentrated under vacuum
  2. washthe solution was washed with H2O
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to dryness
  5. customPurification by flash chromatography on silica gel (4% methanol/CHCl3), trituration
  6. filtrationwith 1:1 ethyl acetate/hexane, filtration
  7. customdrying under vacuum

Sources & evidence

ORD record
ord-c92cece94d45432fa5c4ed366dfbe76e
Source dataset
uspto-grants-2009_04
Patent number
US07524843B2

Reaction notes

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