Sulfuryl chloride → 1-Allyl-cyclopropanesulfonic acid [3,4,6-trifluoro-2-(2-fluoro-4-iodo-phenylamino)phenyl]-amide

HRID 508143

반응식

HRID 508143 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[F:18])[C:3]=1[NH2:19].S(Cl)(Cl)(=O)=O.[CH2:25]([C:28]1([S:31](Cl)(=[O:33])=[O:32])[CH2:30][CH2:29]1)[CH:26]=[CH2:27]>N1C=CC=CC=1>[F:9][C:5]1[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[F:18])=[C:3]([NH:19][S:31]([C:28]2([CH2:25][CH:26]=[CH2:27])[CH2:30][CH2:29]2)(=[O:33])=[O:32])[C:2]([F:1])=[CH:7][C:6]=1[F:8]

참가 물질

5

반응물 3

HCID 24648Sulfuryl chlorideHCID 441819591-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chlorideHCID 593863433,5,6-trifluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine

생성물 1

HCID 576266441-Allyl-cyclopropanesulfonic acid [3,4,6-trifluoro-2-(2-fluoro-4-iodo-phenylamino)phenyl]-amide

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
40 °C

실험 절차

To a stirred solution of the amine, i.e., 3,5,6-trifluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine, (1 eq) in anhydrous pyridine (5 ml/mmole) was added the sulfonyl chloride, i.e., 1-allyl-cyclopropanesulfonyl chloride, (1-5 eq). The reaction mixture was stirred at 40° C. for 48 hours. The reaction mixture was partitioned with water and EtOAc. The organic layer was washed with brine, dried (MGSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica. 1H NMR (CDCl3, 300 MHz): δ 7.41 (dd, 1H), 7.38 (dd, 1H), 7.09 (s, 1H), 6.78 (m, 1H), 6.49 (m, 1H), 5.96 (s, 1H), 5.86 (m, 1H), 5.18 (d, 2H), 2.76 (d, 2H), 1.23 (m, 2H), 0.872 (m, 2H).

후처리

  1. customThe reaction mixture was partitioned with water and EtOAc
  2. washThe organic layer was washed with brine
  3. customdried (MGSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica

출처 및 근거

ORD 기록
ord-182caf2807d84ef799efe0560e10dc7d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09095581B2

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