Chlorosuccinimide → HCID 136337205, 화합물

HRID 1891207노트

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HRID 1891207 반응식
[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

참가 물질

5

반응물 2

HCID 31398ChlorosuccinimideHCID 136337204HCID 136337204, 화합물

생성물 1

HCID 136337205HCID 136337205, 화합물

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-87c41715bf964e01b82f46b36846b6f2
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507512B2

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