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

HRID 547861노트

반응식

HRID 547861 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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]−.

후처리

  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

출처 및 근거

ORD 기록
ord-1dc9bd97c635441184d56f894196e59c
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939569B1

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