Triethylamine → HCID 59608432, compound

HRID 2067157Notes

Reaction equation

HRID 2067157 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([F:19])=[C:14]([CH:18]=2)[C:15]([OH:17])=O)[CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.Cl.[NH2:34][CH2:35][C:36]1[CH:45]=[CH:44][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:38][CH:37]=1>ClCCl.CN(C=O)C.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([F:19])=[C:14]([C:15]([NH:34][CH2:35][C:36]3[CH:37]=[CH:38][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:44][CH:45]=3)=[O:17])[CH:18]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 59608421HCID 59608421, compound

Product 1

HCID 59608432HCID 59608432, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-{[(3-chlorophenyl)methyl]oxy}-2-fluorobenzoic acid (343 mg, 1.22 mmol) in dichloromethane (5 ml) was treated with oxalyl chloride (1.5 eqs, 160 ul, 1.83 mmol) and DMF (1 drop). Effervescence was observed and the mixture was stirred at room temperature for 1 hour. The solvent was then evaporated in vacuo and azeotroped with toluene. A portion of the resulting solid (122 mgs, 0.41 mmol) was dissolved in dichloromethane (5 ml) and treated with triethylamine (2.5 eqs, 142 ul, 1.02 mmol) and methyl 4-(aminomethyl)benzoate hydrochloride (1.5 eqs, 124 mg, 0.61 mmol). The mixture was stirred at room temperature for 18 hours. The mixture was then diluted with methanol and purified by SCX cartridge eluting with methanol. Fractions combined and evaporated to give the title compound as a white solid (227 mg). MS (ES+) m/z 428 [M+H]+ (C23H1935ClFNO4).

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customazeotroped with toluene
  3. stirringThe mixture was stirred at room temperature for 18 hours
  4. custompurified by SCX cartridge
  5. washeluting with methanol
  6. customevaporated

Sources & evidence

ORD record
ord-9c93027ad5394a45b536aff1061c71f6
Source dataset
uspto-grants-2012_10
Patent number
US08293798B2

Reaction notes

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