Dimethyl Sulfoxide → HCID 178438089, compound

HRID 397989Notes

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]([CH2:23][CH3:24])[N:19]=3)[O:12]2)=[C:4]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[N:3]=1.[NH2:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([NH2:38])[CH2:34][CH2:33]1.CS(C)=[O:41]>>[CH:18]([OH:22])=[O:41].[NH2:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([NH:38][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]([CH2:23][CH3:24])[N:19]=4)[O:12]3)=[C:4]([NH:25][CH:26]([CH2:27][CH3:28])[CH2:29][CH3:30])[N:3]=2)[CH2:34][CH2:33]1

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 56625647(2r,3r,4s,5s)-2-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-5-(3-ethyl-[1,2,4]oxadiazol-5-yl)-tetrahydro-furan-3,4-diol

HCID 178511674HCID 178511674, compound2×

Product 1

HCID 178438089HCID 178438089, compound

Conditions

Temperature: 85 °C

Procedure

Intermediate 9 (0.070 g, 0.161 mmol) and trans-1,4-diaminocyclohexane (0.092 g, 0.807 mmol) were dissolved in DMSO (0.03 ml) and heated at 80-90° C. in a sealed vial (eg Reacti vial™), for 66 h, a further portion of trans-1,4-diaminocyclohexane (0.092 mg, 0.807 mmol) was added after the first 20 h. The product was purified by Autoprep. HPLC to give the title compound after freeze drying as a brown solid (0.082 g). LC/MS system B Rt=2.21 min, m/z=516 MH+.

Workup

customThe product was purified by Autoprep

Sources & evidence

ORD record: ord-37cb9e42a06d44d5bd25cb9517bb0f91
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610665B1

Reaction notes

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