2-Chloroadenosine → 2-[2-(p-Cyclohexylvinyl-phenyl)-ethylamino]-adenosine

HRID 1087013Notes

Reaction equation

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

Participants

Reactant 2

HCID 89742-Chloroadenosine

HCID 534075602-[4-(2-Cyclohexyl-vinyl)-phenyl]-ethylamine

Product 1

HCID 679231942-[2-(p-Cyclohexylvinyl-phenyl)-ethylamino]-adenosine

Procedure

Reaction of 2-chloroadenosine with p-(cyclohexylvinyl)phenylethylamine in the manner described e.g. in Example 14 gives 2-[2-(p-cyclohexylvinyl-phenyl)-ethylamino]-adenosine, [alpha]D25 =-26.4° in DMSO, m.p. 161°-164°.

Sources & evidence

ORD record: ord-6e84fc46c5474ec5ad6eb3376a42453f
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05034381

Reaction notes

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