Acetic Anhydride → (2-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-chloropyridin-3-yl)methyl Acetate

HRID 407652Notes

Reaction equation

HRID 407652 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[C:22]([CH2:23][OH:24])=[C:21]([Cl:25])[CH:20]=[CH:19][N:18]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(N(CC)CC)C>[C:26]([O:24][CH2:23][C:22]1[C:17]([N:10]2[N:9]=[CH:8][C:7]3[C:12](=[C:13]([F:15])[CH:14]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=3)[C:11]2=[O:16])=[N:18][CH:19]=[CH:20][C:21]=1[Cl:25])(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 866839406-tert-Butyl-2-(4-chloro-3-(hydroxymethyl)pyridin-2-yl)-8-fluorophthalazin-1(2H)-one

Product 1

HCID 86683941(2-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-chloropyridin-3-yl)methyl AcetateYield 82%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 116a (1.6 g, 4.4 mmol), acetic anhydride (10 mL), and triethylamine (1 mL). The reaction mixture was stirred at room temperature for 1 h and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 30:1 dichloromethane/methanol to afford 116b as a brown solid (1.4 g, 82%). MS: [M+H]+ 404.3.

Workup

  1. customA 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica-gel column chromatography
  4. washeluting with 30:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-a418af6959ec47868e0792ead41b883d
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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