Triethylamine → (2'-[(Methanesulfonyl-phenethyl-amino)-methyl]-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl}-acetic acid methyl ester

HRID 1810331Notes

Reaction equation

HRID 1810331 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][NH:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>C(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:20])[F:22])=[CH:15][C:14]=2[CH2:23][N:24]([S:42]([CH3:41])(=[O:44])=[O:43])[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride3×HCID 66607670[6-Methoxy-2'-(phenethylamino-methyl)-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

Product 1

HCID 66607348(2'-[(Methanesulfonyl-phenethyl-amino)-methyl]-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl}-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To [6-methoxy-2′-(phenethylamino-methyl)-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester (0.068 g, 0.15 mmol) and triethylamine (0.02 mL, 0.16 mmol) in CH2Cl2 (1 mL) was added methanesulfonyl chloride (0.01 mL, 0.16 mmol), and the mixture was stirred for 1 hour. Starting material was still present by analytical LCMS, so additional methanesulfonyl chloride was added, and the reaction was stirred overnight at room temperature. Additional methanesulfonyl chloride and triethylamine was added after 20 hours to push the reaction to completion. The solution was then diluted with CH2Cl2 and H2O, and the aqueous layer was separated and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the title compound.

Workup

  1. additionwas added
  2. stirringthe reaction was stirred overnight at room temperature
  3. customthe reaction to completion
  4. customthe aqueous layer was separated
  5. extractionextracted with CH2Cl2
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-861b544656f24effa5f10c7ee4dc0a03
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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