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

HRID 1921052Notes

Reaction equation

HRID 1921052 reaction equation
C(Cl)CCl.N[C:6]1[C:11](/[CH:12]=[CH:13]/[C:14]([OH:16])=O)=[CH:10][CH:9]=[CH:8][N: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=[N:37]C=2C=1.O.C(N(CC)CC)C>CN(C=O)C>[NH2:37][C:8]1[N:7]=[CH:6][C:11](/[CH:12]=[CH:13]/[C:14]([N:29]([CH3:30])[CH2:28][C:20]2[CH2:21][C:22]3[C:27]([C:19]=2[CH3:18])=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:16])=[CH:10][CH:9]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 221382193-Methyl-2-(methylaminomethyl)indene hydrochlorideHCID 225938113-(2-Amino-3-pyridyl)acrylic acid

Product 1

HCID 22593796(E)-3-[6-aminopyridin-3-yl]-N-methyl-N-(3-methyl-1H-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-(o-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. 0.4 H2O; 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-b68b7db77a0f4b28805bf38f9e839f2e
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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