HCID 58405327, compound → HCID 58405451, compound

HRID 44833Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

The title compound was prepared by dissolving (R)-methyl 1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazole-4-carboxylate (Example 38, 0.51 g, 1.33 mmol) in 2 mL of acetic acid and 0.5 mL of concentrated aqueous HCl and heating the resulting solution to 100° C. for 4 hours. The solution was concentrated under vacuum and co-evaporated from toluene three times and the crude material was purified by preparative HPLC. 1H NMR (CDCl3) δ: 8.73 (s, 1H), 8.50 (s, 1H), 7.78 (s, 1H), 4.44-4.45 (m, 1H), 4.32-4.36 (m, 1H), 3.39 (s, 3H), 1.71-2.17 (m, 10H), and 0.92 ppm (t, J=7.6 Hz, 3H); LCMS: 371.1 m/z (M+H)+; ret. Time: 3.008 min (Analytical Method A).

Workup

concentrationThe solution was concentrated under vacuum
customthe crude material was purified by preparative HPLC

Sources & evidence

ORD record: ord-be3c8205d6884974975dca17f1976345
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541418B2

Reaction notes

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