Chlorosuccinimide → HCID 136337205, compound

HRID 1891207Notes

Reaction equation

HRID 1891207 reaction equation
[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

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 136337204HCID 136337204, compound

Product 1

HCID 136337205HCID 136337205, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-87c41715bf964e01b82f46b36846b6f2
Source dataset
uspto-grants-2013_08
Patent number
US08507512B2

Reaction notes

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