Water → HCID 86686014, compound

HRID 2277719Notes

Reaction equation

HRID 2277719 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:12]1[CH:13]=[N:14][CH:15]=[C:16]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH:17]=1)[C:5]2([CH3:25])[CH3:24].[C:26](Cl)(=[O:28])[CH3:27].O>C(Cl)Cl>[C:26]([N:21]1[CH2:22][CH2:23][N:18]([C:16]2[CH:17]=[C:12]([N:6]3[C:5]([CH3:25])([CH3:24])[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=4)[C:7]3=[O:11])[CH:13]=[N:14][CH:15]=2)[CH2:19][CH2:20]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 86686012HCID 86686012, compound

Product 1

HCID 86686014HCID 86686014, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-3,3-dimethyl-2-(5-piperazin-1-yl-pyridin-3-yl)-2,3-dihydro-isoindol-1-one (52 mg, 0.146 mmol) and TEA (29.5 mg, 0.292 mmol) in DCM (5 mL) was added acetyl chloride (17.2 mg, 0.219 mmol) dropwise at 0° C. After stirring for 1 hour at room temperature, the mixture was treated with water and extracted with DCM. The organic layer was dried over anhy. Na2SO4. After removal of solvent, the residue was purified by preparative HPLC to afford the title compound as a white solid (23 mg, 40%). MS: 399.2 (M+H+).

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was dried over anhy
  3. customAfter removal of solvent
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-19e11730ccf9429885fb0711f3f3a664
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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