1,2-Dichloroethane → HCID 6539890, compound

HRID 1761109Notes

Reaction equation

HRID 1761109 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

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 1038662-Propenoic acid, 3-(4-aminophenyl)-, hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 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 nL) 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% MeOHICH2Cl2) gave the title compound (68 mg, 19%) as a yellow foam: 1 H NMR (360 MHz, DMSO-d6, 330K) δ 7.46 (d, J=7.8 Hz,1H), 7.42 (d, 3=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 C20H21N3O0.20H2O: C, 74.37; H, 6.68; N, 13.01. Found: C, 74.21; H, 6.60; N, 12.80.

Workup

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

Sources & evidence

ORD record
ord-b3fa61e25bee417a83945f08323d37f4
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

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