1,2-Dichloroethane → HCID 66678340, compound

HRID 2404364Notes

Reaction equation

HRID 2404364 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([C:19](=[N:21][OH:22])[NH2:20])[CH:16]=[C:15]([F:23])[C:3]=1[CH2:4][N:5]([CH3:14])[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][C:34]([C:37](O)=O)=[CH:33][C:32]=1[C:40]([F:43])([F:42])[F:41].C(Cl)CCl>C(#N)C.N1C=CC=CC=1>[F:1][C:2]1[CH:18]=[C:17]([C:19]2[N:20]=[C:37]([C:34]3[CH:35]=[CH:36][C:31]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[CH3:24])=[C:32]([C:40]([F:41])([F:43])[F:42])[CH:33]=3)[O:22][N:21]=2)[CH:16]=[C:15]([F:23])[C:3]=1[CH2:4][N:5]([CH3:14])[CH2:6][C:7]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:8]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 594958132'-Methyl-2-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acidHCID 76685322HCID 76685322, compound

Product 1

HCID 66678340HCID 66678340, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of Intermediate 76 (0.148 g, 0.45 mmol) and Intermediate 5 (0.107 mg, 0.375 mmol) in ACN (2.5 mL) was added EDC (0.101 g, 0.53 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with pyridine (2.5 mL) and heated at 150° C. in the microwave for 30 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 8.62 (1H, d, J=1.7 Hz), 8.39 (1H, dd, J=8.0, 1.7 Hz), 7.76 (2H, d, J=7.1 Hz), 7.49 (1H, d, J=8.0 Hz), 7.38-7.22 (3H, m), 7.15 (1H, d, J=7.6 Hz), 3.99 (2H, s), 3.25 (2H, s), 2.45 (3H, s), 2.07 (3H, s), 1.50 (9H, s).

Workup

  1. temperatureheated at 150° C. in the microwave for 30 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-f0e4ac6aabd542c1ba0da247654aa38a
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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