Chlorosuccinimide → HCID 136337205、化合物

HRID 1891207ノート

反応式

HRID 1891207 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:28])=[C:6]([C:8]2[N:13]=[C:12]([N:14]3[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]3)[CH:11]=[CH:10][CH:9]=2)[CH:7]=1.[Cl:29]N1C(=O)CCC1=O>C(#N)C.C(Cl)Cl>[Cl:29][C:4]1[C:5]([OH:28])=[C:6]([C:8]2[N:13]=[C:12]([N:14]3[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]3)[CH:11]=[CH:10][CH:9]=2)[CH:7]=[C:2]([F:1])[CH:3]=1

参加物

5

反応物 2

HCID 31398ChlorosuccinimideHCID 136337204HCID 136337204、化合物

生成物 1

HCID 136337205HCID 136337205、化合物

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of the title compound from Example 2 Step B (1.50 g, 3.79 mmol) in acetonitrile (9.5 mL) was added N-chlorosuccinimide (760 mg, 5.69 mmol), and the resulting mixture was placed in a pre-heated oil bath (90° C.). After 1 h, the reaction mixture was allowed to cool to room temperature, then was diluted with DCM, and the resulting mixture was washed with brine. The organic phase was then concentrated in vacuo. Purification by chromatography on silica gel (0 to 30% EtOAc in hexanes, then 30 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 429.9 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 12.50 (s, 1H), 8.18 (s, 1H, 8.14 (t, J=8.0 Hz, 1H), 7.99 (d, J=8.0 Hz, 1H), 7.58 (d, J=8.0 Hz, 1H), 7.46 (dd, J=9.0, 3.0 Hz, 1H), 7.25 (dd, J=9.0, 3.0 Hz, 1H), 4.40 (q, J=7.0 Hz, 2H), 1.40 (t, J=7.0 Hz, 3H).

後処理

  1. customthe resulting mixture was placed in a pre-heated oil bath
  2. custom(90° C.)
  3. washthe resulting mixture was washed with brine
  4. concentrationThe organic phase was then concentrated in vacuo
  5. customPurification by chromatography on silica gel (0 to 30% EtOAc in hexanes

出典と根拠

ORDレコード
ord-87c41715bf964e01b82f46b36846b6f2
出典データセット
uspto-grants-2013_08
特許番号
US08507512B2

反応ノート

読み込み中…