Methanol → N-[5-(1-aminoethyl)-2-fluorophenyl]methanesulfonamide

HRID 75953노트

반응식

HRID 75953 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:10]\O)/[CH3:9])=[CH:4][C:3]=1[NH:12][S:13]([CH3:16])(=[O:15])=[O:14].[H][H].CO>C1COCC1.[Ni].O>[NH2:10][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:4]=1)[CH3:9]

참가 물질

7

반응물 3

HCID 887MethanolHCID 87395620HCID 87395620, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 67426606N-[5-(1-aminoethyl)-2-fluorophenyl]methanesulfonamide

시약·촉매·용매 3

HCID 935Nickel촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

N-{2-Fluoro-5-[(1Z)—N-hydroxyethanimidoyl]phenyl}methanesulfonamide (Method 62, 200 mg, 812 μmol) was dissolved in 15 ml THF, to which was added Raney nickel 2800 slurry in water (200 μl). The mixture was charged with nitrogen and stirred over 1 atm of hydrogen. After 1 hour, MeOH (4 ml) was added and the reaction mixture was stirred overnight. The following morning the solution was filtered through celite, and the cake washed with MeOH, and the organic layer was concentrated to a yellow solid which was dried under high vacuum (181 mg, 96%). 1H NMR: 1.26 (d, 3H, CH3), 2.92 (s, 3H, SO2Me), 3.33 (HOD), 4.04 (q, 1H, CH), 5.70 (br, 2H, NH2), 7.06-7.16 (m, 2H, Ar), 7.35 (m, 1H, Ar). LC/MS: 0.79 min, 231.08 (M−H)−.

후처리

  1. additionThe mixture was charged with nitrogen
  2. filtrationThe following morning the solution was filtered through celite
  3. washthe cake washed with MeOH
  4. concentrationthe organic layer was concentrated to a yellow solid which
  5. customwas dried under high vacuum (181 mg, 96%)
  6. custom0.79 min, 231.08 (M−H)−

출처 및 근거

ORD 기록
ord-d9c208d1e8a440f9a7322e3619c7c740
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835465B2

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