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

HRID 397979Notes

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][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>CS(C)=O>[CH:18]([OH:22])=[O:36].[CH2:26]([CH:25]([NH:24][C:4]1[N:3]=[C:2]([NH:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]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

Conditions

Temperature: 80 °C

Procedure

Intermediate 11 (0.069 g, 0.163 mmol) and 4-(2-aminoethyl)morpholine (0.107 ml, 0.815 mmol) were dissolved in DMSO (0.03 ml) and heated at 80° C. for 26 h in a sealed vial (eg Reacti vial™), a further portion of 4-(2-aminoethyl)morpholine (0.053 ml, 0.407 mmol) was added after the first 20 h. The product was purified by Autoprep. HPLC to give the title compournd after freeze drying as a brown solid (0.059 g). LC/MS system B Rt=2.19 min, m/z=517MH+.

Workup

customThe product was purified by Autoprep
customHPLC to give the title compournd after freeze
dry with materialdrying as a brown solid (0.059 g)

Sources & evidence

ORD record: ord-ca2a87c4fd9242a1a3b74f18308463b0
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610665B1

Reaction notes

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