1,2-Dichloroethane → HCID 66677759, compound

HRID 2410609Notes

Reaction equation

HRID 2410609 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[C:19](=[N:21][OH:22])[NH2:20])[CH2:5][N:6]([CH3:15])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH3:23][O:24][CH2:25][C:26]1[CH:31]=[C:30]([C:32](O)=O)[CH:29]=[CH:28][C:27]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH3:41].C(Cl)CCl>CC#N.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[C:19]1[N:20]=[C:32]([C:30]2[CH:29]=[CH:28][C:27]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[CH3:41])=[C:26]([CH2:25][O:24][CH3:23])[CH:31]=2)[O:22][N:21]=1)[CH2:5][N:6]([CH3:15])[CH2:7][C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidHCID 76685347HCID 76685347, compound

Product 1

HCID 66677759HCID 66677759, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of Intermediate 65 (0.298 g, 0.91 mmol) and Intermediate 3 (0.79 g, 0.70 mmol) in MeCN (2 mL) was added EDC (0.188 g, 0.98 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with pyridine (2 mL) and heated at 150° C. under microwave irradiation for 20 minutes. The solvent was removed in vacuo and the residue dissolved in DCM. The mixture was washed with water and the organic phase passed through a hydrophobic frit. The solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica, iso-hexane/EtOAc) to afford the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.43 (1H, d, J=1.8 Hz), 8.17 (1H, dd, J=7.9, 1.9 Hz), 7.99 (1H, d, J=7.9 Hz), 7.59 (1H, s), 7.42 (1H, dd, J=8.0, 1.6 Hz), 7.37-7.21 (4H, m), 7.13 (1H, d, J=7.4 Hz), 4.22 (2H, m), 3.75 (2H, s), 3.31 (3H, s), 3.22 (2H, s), 2.41 (3H, s), 2.08 (3H, s), 1.50 (9H, s).

Workup

  1. temperatureheated at 150° C. under microwave irradiation for 20 minutes
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in DCM
  4. washThe mixture was washed with water
  5. customThe solvent was evaporated in vacuo
  6. customThe residue was purified by flash chromatography (silica, iso-hexane/EtOAc)

Sources & evidence

ORD record
ord-4d4492d6802745109f872618c2ab25c2
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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