1,2-Dichloroethane → HCID 9818411, compound

HRID 1921062Notes

Reaction equation

HRID 1921062 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 (23 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 (038 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-3bbe728bd6b04836832c263df0b76f97
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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