1-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chloride → 1-Allyl-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methoxyphenyl)cyclopropane-1-sulfonamide

HRID 240986노트

반응식

HRID 240986 반응식
[F:1][C:2]1[C:7]([F:8])=[C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=2[F:17])[C:5]([NH2:18])=[C:4]([O:19][CH3:20])[CH:3]=1.[CH2:21]([C:24]1([S:27](Cl)(=[O:29])=[O:28])[CH2:26][CH2:25]1)[CH:22]=[CH2:23]>N1C=CC=CC=1>[CH2:21]([C:24]1([S:27]([NH:18][C:5]2[C:4]([O:19][CH3:20])=[CH:3][C:2]([F:1])=[C:7]([F:8])[C:6]=2[NH:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=2[F:17])(=[O:29])=[O:28])[CH2:26][CH2:25]1)[CH:22]=[CH2:23]

참가 물질

4

반응물 2

HCID 441819591-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chlorideHCID 532609665,6-difluoro-N1-(2-fluoro-4-iodophenyl)-3-methoxybenzene-1,2-diamine

생성물 1

HCID 574300741-Allyl-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methoxyphenyl)cyclopropane-1-sulfonamide

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
40 °C

실험 절차

To a stirred solution of 5,6-difluoro-N1-(2-fluoro-4-iodophenyl)-3-methoxybenzene-1,2-diamine (1 eq) in anhydrous pyridine (5 ml/mmole) was added 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 ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica to obtain the title product. 1H NMR (CDCl3, 300 MHz): δ 7.417 (dd, 1H), 7.309 (s, 1H), 7.25 (m, 1H), 6.89 (m, 1H), 6.52 (m, 1H), 6.427 (m, 1H), 6.03 (s, 1H), 5.668 (m, 1H), 5.11 (t, 1H), 3.9 (s, 3H), 2.75 (d, 2H), 1.21 (m, 2H), 0.767 (m, 2H).

후처리

  1. customThe reaction mixture was partitioned with water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica

출처 및 근거

ORD 기록
ord-af8c8e90e53f41d2ad689b39591bee8b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648116B2

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