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

HRID 397985Notes

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][CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>CS(C)=O>[CH:18]([OH:22])=[O:37].[CH2:23]([C:20]1[N:19]=[C:18]([C@@H:13]2[C@@H:14]([OH:17])[C@@H:15]([OH:16])[C@H:11]([N:8]3[CH:7]=[N:6][C:5]4[C:9]3=[N:10][C:2]([NH:31][CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[N:3][C:4]=4[NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[O:12]2)[O:22][N:21]=1)[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

Intermediate 9 (0.070 g, 0.161 mmol) and 4-(2-aminoethyl)morpholine (0.106 ml, 0.807 mmol) were dissolved in DMSO (0.03 ml) and heated at 80° C. in a sealed vial (eg Reacti vial™), for 26 h, a further portion of 4-(2-aminoethyl)morpholine (0.053 ml, 0.403 mmol) was added after the first 6 h. The product was purified by Autoprep. HPLC to give the title compound after freeze drying as a beige solid (0.049 g). LC/MS system B Rt=2.27 min, m/z=532 MH+.

Workup

customThe product was purified by Autoprep

Sources & evidence

ORD record: ord-e0f2317e47534460bbd6f9b364e92531
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610665B1

Reaction notes

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