Pyridine → HCID 68954487, compound

HRID 1455839Notes

Reaction equation

HRID 1455839 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]([OH:17])=O)=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.N1C=CC=CC=1.[CH2:32]([O:34][C:35]([C:37]1[N:38]([CH3:48])[C:39]2[C:44]([C:45]=1[Cl:46])=[CH:43][C:42]([NH2:47])=[CH:41][CH:40]=2)=[O:36])[CH3:33]>C(Cl)Cl.CN(C=O)C>[CH2:32]([O:34][C:35]([C:37]1[N:38]([CH3:48])[C:39]2[C:44]([C:45]=1[Cl:46])=[CH:43][C:42]([NH:47][C:15]([C:10]1[C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:18])=[CH:8][CH:7]=3)=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:17])=[CH:41][CH:40]=2)=[O:36])[CH3:33]

Participants

7

Reactant 4

HCID 1049PyridineHCID 552514'-(Trifluoromethyl)(1,1'-biphenyl)-2-carboxylic acidHCID 65578Oxalyl chlorideHCID 69142509HCID 69142509, compound

Product 1

HCID 68954487HCID 68954487, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

4′-Trifluoromethyl-2-biphenylcarboxylic acid was converted to the corresponding acid chloride by treatment with oxalyl chloride in methylene chloride in the presence of catalytic amount of DMF. To a solution of the acid chloride (10.8 g, 38 mmol) and pyridine (3.27 mL, 40 mmol) in methylene chloride (200 mL) was added the product of step (c) (10.1 g, 40 mmol), and the reaction mixture was stirred at room temperature for 1 hour. The reaction solution was diluted to 600 mL with CH2Cl2, washed with 0.1 N HCl solution (2×500 mL) and with brine (500 mL), and then dried (MgSO4). The solvent was evaporated in vacuo to give the crude product which was purified by recrystallization from EtOAc/isooctane to afford 13.8 g of the title compound.

Workup

  1. washwashed with 0.1 N HCl solution (2×500 mL) and with brine (500 mL)
  2. dry with materialdried (MgSO4)
  3. customThe solvent was evaporated in vacuo
  4. customto give the crude product which
  5. customwas purified by recrystallization from EtOAc/isooctane

Sources & evidence

ORD record
ord-aebf058fb60a4cdd9351c61989bd274b
Source dataset
uspto-grants-2009_01
Patent number
US07482368B2

Reaction notes

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