Water → HCID 9885349, compound

HRID 1166064Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]1[O:8][N:7]=[C:6]([C:9]2[N:13]3[NH:14][C:15](=[O:22])[C:16]4[C:21]([C:12]3=[N:11][N:10]=2)=[CH:20][CH:19]=[N:18][CH:17]=4)[CH:5]=1.Cl[CH2:24][C:25]1[N:26]=[N:27][N:28]([CH3:30])[CH:29]=1.O>CN(C=O)C>[CH3:3][C:4]1[O:8][N:7]=[C:6]([C:9]2[N:13]3[N:14]=[C:15]([O:22][CH2:24][C:25]4[N:26]=[N:27][N:28]([CH3:30])[CH:29]=4)[C:16]4[C:21]([C:12]3=[N:11][N:10]=2)=[CH:20][CH:19]=[N:18][CH:17]=4)[CH:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium hydride (42 mg of a 60% dispersion on oil, 1.1 mmol) was added to a stirred solution of 3-(5-methylisoxazol-3-yl)-1,2,3a,4,7-pentaazacyclopenta[a]naphthalen-5(4H)-one (200 mg, 0.75 mmol) in DMF (6 ml) at room temperature under nitrogen, and the mixture was heated at 60° C. for 0.5 h. The reaction mixture was allowed to cool to room temperature, treated with 4-chloromethyl-1-methyl-1,2,3-triazole (108 mg, 0.82 mmol) and heated at 60° C. for 1.5 h. On cooling to room, water was added. The mixture was extracted with ethyl acetate, the organics separated, dried (MgSO4), and evaporated in vacuo. The residue was recrystallised from methanol to afford the title product as a white solid (39 mg, 14%), 1H NMR (360 MHz, d6 DMSO) δ 2.60 (3H, s, Ar—CH3), 4.08 (3H, s, N—CH3), 5.73 (2H, s, OCH2), 7.21 (1H, d, J=0.8 Hz, Ar—H), 8.45 (2H, m, Ar—H), 9.15 (1H, d, J=5.3 Hz, Ar—H)), 9.41 (1H, s, Ar—H); MS (ES+) m/e 364 [MH]+.

Workup

temperatureto cool to room temperature
temperatureheated at 60° C. for 1.5 h
additionwas added
extractionThe mixture was extracted with ethyl acetate
dry with materialthe organics separated, dried (MgSO4)
customevaporated in vacuo
customThe residue was recrystallised from methanol

Sources & evidence

ORD record: ord-b3bfbd2362724da0b7d1082c47bfef86
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613766B1

Reaction notes

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