1,2-Dichloroethane → HCID 6539890, compound

HRID 2112694Notes

Reaction equation

HRID 2112694 reaction equation
C(Cl)CCl.Cl.[NH2:6][C:7]1[CH:17]=[CH:16][C:10]([CH:11]=[CH:12][C:13]([OH:15])=O)=[CH:9][CH:8]=1.[CH3:18][N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH: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>[NH2:6][C:7]1[CH:8]=[CH:9][C:10](/[CH:11]=[CH:12]/[C:13]([N:29]([CH3:30])[CH2:28][C:20]2[N:19]([CH3:18])[C:27]3[C:22]([CH:21]=2)=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:15])=[CH:16][CH:17]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 1038662-Propenoic acid, 3-(4-aminophenyl)-, hydrochlorideHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amine

Product 1

HCID 6539890HCID 6539890, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (218 mg, 1.14 mmole) was added to a solution of 4-aminocinnamic acid hydrochloride (220 mg, 1.10 mmole), 1-methyl-2-(methylaminomethyl)-1H-indole (0.20 g, 1.15 mmole), HOBt.H2O (154 mg, 1.14 mmole), and triethylamine (0.20 mL, 1.43 mmole) in DMF (20 mL) at RT. The reaction was stirred overnight, then was concentrated in vacuo. The residue was diluted with 5% NaHCO3 and extracted with CH2Cl2. The combined organic extracts were washed with brine (2×30 mL) and dried over MgSO4. Flash chromatography on silica gel (3% MeOH/CH2Cl2) gave the title compound (68 mg, 19%) as a yellow foam: 1H NMR (360 MHz, DMSO-d6, 330K) δ 7.46 (d, J=7.8 Hz, 1H), 7.42 (d, J=15.3 Hz, 1H), 7.37 (d, J=8.3 Hz, 1H), 7.32 (d, J=8.5 Hz, 2H), 7.06-7.15 (m, 1H), 6.94-7.03 (m, 1H), 6.81 (d, J=15.3 Hz, 1H), 6.58 (d, J=8.5 Hz, 2H), 6.33 (s, 1H), 5.25 (br s, 2H), 4.85 (s, 2H), 3.70 (s, 3H), 3.02 (s, 3H); MS (ES) m/e 320 (M+H)+. Anal. Calcd for C20H21N3O.0.20H2O: C, 74.37; H, 6.68; N, 13.01. Found: C, 74.21; H, 6.60; N, 12.80.

Workup

  1. customat RT
  2. concentrationwas concentrated in vacuo
  3. additionThe residue was diluted with 5% NaHCO3
  4. extractionextracted with CH2Cl2
  5. washThe combined organic extracts were washed with brine (2×30 mL)
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-d99b22eca50c469b8f6fcac44d530225
Source dataset
uspto-grants-2009_04
Patent number
US07524843B2

Reaction notes

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