Acetyl chloride → HCID 86686022, compound

HRID 2277727Notes

Reaction equation

HRID 2277727 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:17]=[N:16][CH:15]=[C:14]([CH:18]3[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]3)[N:13]=1)[C:5]2([CH3:25])[CH3:24].CCN(CC)CC.[C:33](Cl)(=[O:35])[CH3:34]>C(Cl)Cl>[C:33]([N:20]1[CH2:21][CH2:22][CH2:23][CH:18]([C:14]2[N:13]=[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:17]=[N:16][CH:15]=2)[CH2:19]1)(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86686021HCID 86686021, compound

Product 1

HCID 86686022HCID 86686022, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-chloro-3,3-dimethyl-2-(6-piperidin-3-yl-pyrazin-2-yl)-2,3-dihydro-isoindol-1-one (80 mg, 0.22 mmol) and Et3N (44.4 mg, 0.44 mmol) in DCM (2 mL) was added acetyl chloride (26.4 mg, 0.34 mmol) at 0° C. After removal of solvent, the residue was purified by prep-HPLC to yield the title compound (30.6 mg, 35%) as a white solid. MS: 399.2 (M+H+).

Workup

  1. customAfter removal of solvent
  2. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-4efaae6dc60c4e0fba53103b158720e0
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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