Dimethyl Sulfoxide → (2r,3r,4s,5s)-2-[6-(1-Ethyl-propylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-tetrahydro-furan-3,4-diol formate

HRID 397984Notes

Reaction equation

HRID 397984 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.[N:30]1([CH2:36][CH2:37][NH2:38])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.CS(C)=[O:41]>>[CH:18]([OH:22])=[O:41].[CH2:26]([CH:25]([NH:24][C:4]1[N:3]=[C:2]([NH:38][CH2:37][CH2:36][N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[C@H:11]1[C@H:15]([OH:16])[C@H:14]([OH:17])[C@@H:13]([C:18]2[O:22][N:21]=[C:20]([CH3:23])[N:19]=2)[O:12]1)[CH2:28][CH3:29])[CH3:27]

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 33944N-(2-Aminoethyl)piperidine2×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

Product 1

HCID 70021678(2r,3r,4s,5s)-2-[6-(1-Ethyl-propylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-tetrahydro-furan-3,4-diol formate

Procedure

Intermediate 11 (0.069 g, 0.163 mmol) and 2-piperidinoethylamine (0.116 ml, 0.815 mmol) were dissolved in DMSO (0.03 ml) and heated at 80° C. for 40 h in a sealed vial (Reacti vial™) a further portion of 2-piperidinoethylamine (0.058 ml, 0.407 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 (0.031 g). LC/MS system B Rt=2.25 min, m/z=516 MH+.

Workup

  1. additionwas added after the first 20 h
  2. customThe product was purified by Autoprep

Sources & evidence

ORD record
ord-c01a3797b2964d078a784360bc103255
Source dataset
uspto-grants-2003_08
Patent number
US06610665B1

Reaction notes

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