Dimethyl Sulfoxide → HCID 178446277, compound

HRID 397983Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[C@H:15]([OH:16])[C@H:14]([OH:17])[C@@H:13]([C:18]3[O:22][N:21]=[C:20]([CH3:23])[N:19]=3)[O:12]2)=[C:4]([NH:24][CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[N:3]=1.[NH2:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([NH2:37])[CH2:33][CH2:32]1.CS(C)=[O:40]>>[CH:18]([OH:22])=[O:40].[NH2:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([NH:37][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[C@H:11]3[C@H:15]([OH:16])[C@H:14]([OH:17])[C@@H:13]([C:18]4[O:22][N:21]=[C:20]([CH3:23])[N:19]=4)[O:12]3)=[C:4]([NH:24][CH:25]([CH2:26][CH3:27])[CH2:28][CH3:29])[N:3]=2)[CH2:33][CH2:32]1

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 56619484(2r,3r,4s,5s)-2-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-tetrahydro-furan-3,4-diol

HCID 178511674HCID 178511674, compound2×

Product 1

HCID 178446277HCID 178446277, compound

Conditions

Temperature: 85 °C

Procedure

Intermediate 11 (0.069 g, 0.163 mmol) and trans-1,4-diaminocyclohexane (0.093 g, 0.815 mmol) were dissolved in DMSO (0.03 ml) and heated at 80-90° C. for 66 h in a sealed vial (eg Reacti vial™), a further portion of trans-1,4-diaminocyclohexane (0.093 g, 0.815 mmol) was added after the first 20 h. The product was purified by Autoprep. to give the title compound after freeze drying as a brown solid (0.063 g). LC/MS system B Rt=2.12 min, m/z=502 MH+.

Workup

customThe product was purified by Autoprep

Sources & evidence

ORD record: ord-fb19eab08b354a9ba28a1f0da9511c21
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610665B1

Reaction notes

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