1,2-Dichloroethane → (E)-3-[6-aminopyridin-3-yl]-N-methyl-N-(3-methyl-4H-inden-2-ylmethyl)acrylamide

HRID 2112704Notes

Reaction equation

HRID 2112704 reaction equation
C(Cl)CCl.[NH2:5][C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([OH:16])=O)=[CH:8][CH:7]=1.Cl.[CH3:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][C:20]=1[CH2:28][NH:29][CH3:30].C1C=CC2N(O)N=NC=2C=1.O.C(N(CC)CC)C>CN(C=O)C>[NH2:5][C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([N:29]([CH3:30])[CH2:28][C:20]2[C:19]([CH3:18])=[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH2:26]3)[CH:21]=2)=[O:16])=[CH:8][CH:7]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidHCID 221382193-Methyl-2-(methylaminomethyl)indene hydrochloride

Product 1

HCID 57440847(E)-3-[6-aminopyridin-3-yl]-N-methyl-N-(3-methyl-4H-inden-2-ylmethyl)acrylamideYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (0.383 g, 2.0 mmole) was added to a solution of (E)-3-(6-aminopyridin-3-yl)acrylic acid (0.328 g, 2.0 mmole), 3-methyl-2-(methylaminomethyl)indene hydrochloride (0.420 g, 2.0 mmole), HOBt.H2O (0.306 g, 2.0 mmole), and triethylamine (0.57 mL, 4.0 mmole) in anhydrous DMF (18 mL) at RT. The reaction was stirred overnight and concentrated in vacuo. The residue was diluted with 5% NaHCO3 and extracted with CH2Cl2. The combined organic extracts were washed with brine and dried over MgSO4. Flash chromatography on silica gel (3% MeOH/CH2Cl2) gave the title compound (0.33 g, 52%) as a colorless solid: MS (ES) m/e 320.2 (M+H)+. Anal. Calcd for C20H21N3O.0.4H2O: C, 73.57; H, 6.72; N, 12.86. Found: C, 73.94; H, 6.92; N, 12.50.

Workup

  1. customat RT
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with 5% NaHCO3
  4. extractionextracted with CH2Cl2
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-e49c1fe45e364d1f9ff39b85ee9e1152
Source dataset
uspto-grants-2009_04
Patent number
US07524843B2

Reaction notes

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