1,2-Dichloroethane → HCID 6539891, compound

HRID 1921041Notes

Reaction equation

HRID 1921041 reaction equation
C(Cl)CCl.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7](/[CH:11]=[CH:12]/[C:13]([OH:15])=O)[CH:6]=1.[CH3:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]1[CH2:26][NH:27][CH3:28].C1C=CC2N(O)N=NC=2C=1.O>CN(C=O)C>[CH3:28][N:27]([CH2:26][C:18]1[N:17]([CH3:16])[C:25]2[C:20]([CH:19]=1)=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13](=[O:15])/[CH:12]=[CH:11]/[C:7]1[CH:6]=[N:5][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 776396trans-3-(3-Pyridyl)acrylic acidHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amine

Product 1

HCID 6539891HCID 6539891, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (0.22 g, 1.14 mmole) was added to a solution of trans-3-(3-pyridyl)acrylic acid (0.17 g, 1.14 mmole), 1-methyl-2-(methylaminomethyl)-1H-indole (0.20 g, 1.15 mmole), and HOBt.H2O (0.15 g, 1.11 mmole) in DMF (10 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 and dried over MgSO4. Flash chromatography on silica gel (3% MeOH/CH2Cl2) followed by preparative TLC (3% MeOH/CH2Cl2) gave the title compound (0.14 g, 40%) as a white solid: 1H NMR (360 MHz, CDCl3) indicated an approximately 8:1 mixture of amide rotamers; for the major rotamer. δ 8.79 (s, 1H), 8.59 (d, J=3.9 Hz, 1H), 7.84 (d, J 7.6 Hz, 1H), 7.76 (d, J=15.5 Hz, 1H), 7.59 (d, J=7.8 Hz, 1H), 7.38-7.48 (m, 2H), 7.19-7.27 (m, 1H), 7.08-7.17 (m, 1H), 6.98 (d, J=15.5 Hz, 1H), 6.51 (s, 1H), 4.94 (s, 2H), 3.73 (s, 3H), 3.09 (s, 3H); MS (ES) m/e 306 (M+H)+. Anal. Calcd for C19H19N3O. 0.20 H2O: C, 73.86; H, 6.33; N, 13.60. Found: C, 73.52; H, 6.32; N, 13.43.

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
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-e289e83ae82245e4814f81f292cd985c
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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