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

HRID 1774632Notes

Reaction equation

HRID 1774632 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(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34]>O1CCCC1>[C:33]([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:35])[CH3:34]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471Triethylamine2×HCID 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 Acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 6-tert-butyl-2-(4-chloro-3-(hydroxymethyl)pyridin-2-yl)-8-fluorophthalazin-1(2H)-one 104a (150 mg, 0.42 mmol) and triethylamine, Et3N (0.12 mL, 0.84 mmol) in tetrahydrofuran, THF (2.5 mL) was added acetyl chloride, AcCl (44 μl, 0.62 mmol). The mixture was stirred at rt for 1 h and quenched with water, extracted with ethylacetate, EA. The combined organic layers were dried over Na2SO4, filtered and concentrated to give 104b (160 mg) as a colorless oil. MS-ESI: [M+H]+ 404.1

Workup

  1. customquenched with water
  2. extractionextracted with ethylacetate, EA
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1133c0c127b04711ba659112d2b9ae39
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

Loading…