1,2-Dichloroethane → HCID 9798694, compound

HRID 1581685Notes

Reaction equation

HRID 1581685 reaction equation
C(Cl)CCl.[C:5]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]([C:11]([OH:13])=O)=[CH:7][CH:8]=[CH:9][CH:10]=1.[CH3:20][N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:22]1[CH2:30][NH:31][CH3:32].C1C=CC2N(O)N=NC=2C=1.O>CN(C=O)C>[CH3:32][N:31]([CH2:30][C:22]1[N:21]([CH3:20])[C:29]2[C:24]([CH:23]=1)=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:11](=[O:13])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 962WaterHCID 70357o-Phenylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amine

Product 1

HCID 9798694HCID 9798694, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (0.22 g, 1.14 mmole) was added to a solution of 2-biphenylcarboxylic acid (0.22 g, 1.14 mmole), 1-methyl-2-(methylaminomethyl)indole (0.20 g, 1.15 mmole), and HOBt.H2O (0.15 g, 1.11 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 and dried over MgSO4. Flash chromatography on silica gel (3% MeOH/CH2Cl2) followed by preparative TLC (3% MeOH/CH2Cl2) gave the title compound (0.10 g, 25%) as a light yellow solid: 1H NMR (360 MHz, CDCl3) indicated an approximately 5:1 mixture of amide rotamers; for the major rotamer: δ 7.03-7.58 (m, 13H), 6.19 (s, 1H), 4.50 -5.00 (m, 2H), 3.57 (s, 3H), 2.40 (s, 3H); for the minor rotamer: δ 7.03-7.58 (m, 13H), 6.14 (s, 1H), 4.50-5.00 (m, 2H), 3.38 (s, 3H), 2.76 (s, 3H); MS (ES) m/e 356 (M+H)+. Anal. Calcd for C24H22N2O.0.80H2O: C, 78.15; H, 6.45; N, 7.59. Found: C, 77.96; H, 6.29; N, 7.35.

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-0af47ba5b8734d2e9434bb4f573281ea
Source dataset
uspto-grants-2004_05
Patent number
US06730684B1

Reaction notes

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