Potassium Carbonate → HCID 9950805, compound

HRID 496554Notes

Reaction equation

[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[N:11]3[NH:12][C:13](=[O:20])[C:14]4[C:19]([C:10]3=[N:9][CH:8]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:3]=1.[H-].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:31][C:32]1[N:33]=[N:34][N:35]([CH3:37])[CH:36]=1>CN(C=O)C.O>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[N:11]3[N:12]=[C:13]([O:20][CH2:31][C:32]4[N:33]=[N:34][N:35]([CH3:37])[CH:36]=4)[C:14]4[C:19]([C:10]3=[N:9][CH:8]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3-(5-Methylisoxazol-3-yl)imidazo[2,1-a]phthalazin-6-one (100 mg, 0.375 mmol) was suspended in DMF (5 ml) and sodium hydride (60% dispersion in oil, 33 mg, 0.83 mmol) was added. After stirring at room temperature for 10 minutes potassium carbonate (50 mg, 0.36 mmol) was added, followed by 4-chloromethyl-1-methyl triazole hydrochloride (69 mg, 0.41 mmol). The solution was heated at 80° C. for 4 hours, then cooled and poured into water. The solid product was filtered off and washed with water and hexane. The solid was recrystallised from ethyl acetate/hexane to yield the title compound (83 mg, 62%), 1H NMR (360 MHz, CDCl3) 2.55 (3H, s), 4.11 (3H, s), 5.75 (2H, s), 6.72 (1H, s), 7.67 (1H, t), 7.86 (1H, t), 7.99 (1H, s), 8.17 (2H, d), 8.51 (1H, d); MS+362 [MH]+.

Workup

additionwas added
temperaturecooled
filtrationThe solid product was filtered off
washwashed with water and hexane
customThe solid was recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record: ord-75a227f680694b44988544ec3f1fe68a
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06946461B2

Reaction notes

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