Acetyl chloride → HCID 86686007, compound

HRID 2277716Notes

Reaction equation

HRID 2277716 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([C:19]1[CH:20]=[N:21][CH:22]=[C:23]([O:25][CH:26]3[CH2:30][CH2:29][NH:28][CH2:27]3)[CH:24]=1)[C:12]2([CH3:32])[CH3:31].CCN(CC)CC.C(Cl)(=O)C>O>[C:3]([N:28]1[CH2:29][CH2:30][CH:26]([O:25][C:23]2[CH:24]=[C:19]([N:13]3[C:12]([CH3:32])([CH3:31])[C:11]4[C:15](=[CH:16][CH:17]=[C:9]([Cl:8])[CH:10]=4)[C:14]3=[O:18])[CH:20]=[N:21][CH:22]=2)[CH2:27]1)(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86686008HCID 86686008, compound

Product 1

HCID 86686007HCID 86686007, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-chloro-3,3-dimethyl-2-[5-(pyrrolidin-3-yloxy)-pyridin-3-yl]-2,3-dihydro-isoindol-1-one trifluoro acetic acid salt (94.2 mg, 0.2 mmol) was added Et3N (1 mmol) and acetyl chloride (23.4 mg, 0.3 mmol) at 0° C. The resulting reaction mixture was stirred at room temperature for 1 hour before it was poured into H2O (1 mL) and extracted with EtOAc (15 mL×2). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by PrepHPLC to give the title compound (25.5 mg, 35%) as a white solid. MS: 400.2 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc (15 mL×2)
  3. washThe combined organic layers were washed with brine
  4. customdried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo
  7. customto give a crude product which
  8. customwas purified by PrepHPLC

Sources & evidence

ORD record
ord-f101752715344930a6ba02b1c0583ae4
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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