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

HRID 75953ノート

反応式

HRID 75953 の反応式
[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]

参加物

7

反応物 3

HCID 887MethanolHCID 87395620HCID 87395620、化合物HCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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)−.

後処理

  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)−

出典と根拠

ORDレコード
ord-d9c208d1e8a440f9a7322e3619c7c740
出典データセット
uspto-grants-2014_09
特許番号
US08835465B2

反応ノート

読み込み中…