2-Thiophenecarboxylic acid → 8-Chloro-3-pentyl-1-{4-[5-(2-thienyl)-1,2,4-oxadiazol-3-yl]butyl}-3,7-dihydro-1H-purine-2,6-dione

HRID 1097696Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.[Cl:9][C:10]1[NH:18][C:17]2[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH2:22][CH2:23]/[C:24](=[N:27]/[H])/[NH:25]O)[C:14](=[O:29])[N:13]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:12]=2[N:11]=1>CN1C(=O)CCC1>[Cl:9][C:10]1[NH:18][C:17]2[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]3[N:25]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[O:8][N:27]=3)[C:14](=[O:29])[N:13]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:12]=2[N:11]=1

Participants

Conditions

Temperature: 150 °C

Procedure

2-Thiophenecarboxylic acid (14 mg, 0.11 mmol) was dissolved in NMP (0.9 ml) and treated with CDl (18 mg, 0.11 mmol). After 1 h, (1Z)-5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)-N-hydroxypentanimidamide (50 mg, 0.13 mmol) was added and the mixture heated in the microwave at 150° C. for 15 min. The solution was directly purified by MDAP to obtain the title compound which was then freeze dried from 1,4-dioxane to give the title compound as a white solid (19 mg, 31%).

Workup

additiontreated with CDl (18 mg, 0.11 mmol)
customThe solution was directly purified by MDAP

Sources & evidence

ORD record: ord-18bb2147afe44699b8e68f81a2f1d588
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143264B2

Reaction notes

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