Pyridine → HCID 71008485, compound

HRID 1025578Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[CH2:23][OH:24])[N:9]([CH3:25])[CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[C:26](OC(=O)C)(=[O:28])[CH3:27].N1C=CC=CC=1>ClCCl>[C:26]([O:24][CH2:23][C:17]1[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:16]=1[N:10]1[N:9]([CH3:25])[CH2:8][C:7]2[C:12](=[CH:13][CH:14]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=2)[C:11]1=[O:15])(=[O:28])[CH3:27]

Participants

Conditions

Temperature: 45 °C

Procedure

In a 100 mL round-bottomed flask, 6-tert-butyl-2-(3-chloro-2-(hydroxymethyl)phenyl)-3-methyl-3,4-dihydrophthalazin-1(2H)-one (500 mg, 1.39 mmol, Eq: 1.00), acetic anhydride (711 mg, 657 μl, 6.97 mmol, Eq: 5) and pyridine (331 mg, 338 μl, 4.18 mmol, Eq: 3) were combined with dichloromethane (10.0 ml) to give a colorless solution. The reaction mixture was heated to 45° C. and stirred for 8 h. Cooled to room temperature and stirred for 48 h. The crude reaction mixture was concentrated in vacuo to a tan oil. The crude material was purified by flash chromatography (silica gel, 20%-30% ethyl acetate/hexanes gradient) to give 2-(6-tert-butyl-3-methyl-1-oxo-3,4-dihydrophthalazin-2(1H)-yl)-6-chlorobenzyl acetate (489 mg, 88%): 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.37 (s, 9H) 2.03 (s, 3H) 2.62 (s, 3H) 4.45 (s, 2H) 5.33 (s, 2H) 7.23 (d, J=1.51 Hz, 1H) 7.35-7.39 (m, 2H) 7.43-7.52 (m, 2H) 8.03 (d, J=8.31 Hz, 1H).

Workup

customto give a colorless solution
temperatureCooled to room temperature
stirringstirred for 48 h
customThe crude reaction mixture
concentrationwas concentrated in vacuo to a tan oil
customThe crude material was purified by flash chromatography (silica gel, 20%-30% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record: ord-0a5860edd25b43df94200460128d3428
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729078B2

Reaction notes

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