2-(1-Hydroxy-ethyl)-7-(tetrahydro-pyran-4-yl)-3H-imidazo[5,1-f][1,2,4]triazin-4-one → HCID 136592756, compound

HRID 57733Notes

Reaction equation

[OH:1][CH:2]([C:4]1[NH:9][C:8](=[O:10])[C:7]2=[CH:11][N:12]=[C:13]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:6]2[N:5]=1)[CH3:3]>C(Cl)Cl.O=[Mn]=O>[C:2]([C:4]1[NH:9][C:8](=[O:10])[C:7]2=[CH:11][N:12]=[C:13]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:6]2[N:5]=1)(=[O:1])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of compound 14 (400 mg, 1.6 mmol) in CH2Cl2 (50 mL) was added MnO2 (520 mg, 6 mmol). The mixture was heated at 50° C. overnight. The reaction mixture was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford compound 15 (370 mg, 86% yield) as a white solid. LC-MS: m/z 263 [M+H]+. 1H NMR (300 MHz, CDCl3): δ 8.99 (br. s, 1H), 7.93 (s, 1H), 4.16˜4.12 (m, 2H), 3.67˜3.59 (m, 2H), 3.54˜3.48 (m, 1H), 2.72 (s, 3H), 2.19˜2.11 (m, 2H), 2.00˜1.96 (m, 2H).

Workup

filtrationThe reaction mixture was filtered
washwashed with ethyl acetate
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-941f8a23cd834f358fec15525228006d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434733B2

Reaction notes

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