Triethylamine → N-[3-(2',4',5'-trifluoro-biphenyl-4-yloxymethyl)-phenyl]-methanesulfonamide

HRID 547861Notes

Reaction equation

HRID 547861 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([F:9])[C:6]([F:10])=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:20]=[C:21]([NH2:25])[CH:22]=[CH:23][CH:24]=2)=[CH:13][CH:12]=1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>N1C=CC=CC=1>[F:2][C:3]1[CH:8]=[C:7]([F:9])[C:6]([F:10])=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:20]=[C:21]([NH:25][S:34]([CH3:33])(=[O:36])=[O:35])[CH:22]=[CH:23][CH:24]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 671537603-(2',4',5'-Trifluoro-biphenyl-4-yloxymethyl)-phenylamine hydrochloride

Product 1

HCID 52920349N-[3-(2',4',5'-trifluoro-biphenyl-4-yloxymethyl)-phenyl]-methanesulfonamideYield 56.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(2′,4′,5′-trifluoro-biphenyl-4-yloxymethyl)-phenylamine hydrochloride (76 mg, 0.209 mmol), triethylamine (29 uL, 0.209 mmol) and methanesulfonyl chloride (19.3 uL, 0.249 mmol) in dry pyridine (3 mL) was stirred at ice bath temperature for 1 hr and then at RT for 2 hrs. The reaction mixture was evaporated, re-evaporated from toluene, dissolved in EtOAc, washed with H2O, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography with a 0-25% gradient of ethyl acetate in hexanes and lyophilized to yield 48 mg of N-[3-(2′,4′,5′-trifluoro-biphenyl-4-yloxymethyl)-phenyl]-methanesulfonamide as a white amorphous powder. LC-MS (ES) calculated for C20H16F3NO3S, 407.41; found m/z 406 [M−H]−.

Workup

  1. customThe reaction mixture was evaporated
  2. customre-evaporated from toluene
  3. dissolutiondissolved in EtOAc
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography with a 0-25% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1dc9bd97c635441184d56f894196e59c
Source dataset
uspto-grants-2011_05
Patent number
US07939569B1

Reaction notes

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