4-ethyl-2H-1,2,3-Triazole → 3-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-ethyl-[1,2,3]triazol-1-yl)-cyclopentane-1,2-diol

HRID 1641889Notes

Reaction equation

HRID 1641889 reaction equation
[CH2:1](OC(=O)O[C@H]1C[C@@H](N2C=NC3C2=NC(Cl)=NC=3Cl)C=C1)C.[Cl:23][C:24]1[N:32]=[C:31]2[C:27]([N:28]=[CH:29][N:30]2[C@@H:33]2[CH2:37][C@H:36]([N:38]3[N:42]=[N:41][C:40]([CH2:43][CH3:44])=N3)[C@@H:35]([OH:45])[C@H:34]2[OH:46])=[C:26]([NH:47][CH2:48][CH:49]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[N:25]=1.C(C1C=NNN=1)C>>[Cl:23][C:24]1[N:32]=[C:31]2[C:27]([N:28]=[CH:29][N:30]2[CH:33]2[CH2:37][CH:36]([N:38]3[CH:1]=[C:40]([CH2:43][CH3:44])[N:41]=[N:42]3)[CH:35]([OH:45])[CH:34]2[OH:46])=[C:26]([NH:47][CH2:48][CH:49]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[N:25]=1

Participants

4

Reactant 3

HCID 147949874-ethyl-2H-1,2,3-TriazoleHCID 58025019Carbonic acid (1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl ester ethyl esterHCID 86622803(1R,2S,3R,5S)-3-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(5-ethyl-tetrazol-2-yl)-cyclopentane-1,2-diol

Product 1

HCID 866228023-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-ethyl-[1,2,3]triazol-1-yl)-cyclopentane-1,2-diol

Procedure

This compound is prepared from carbonic acid (1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester (Intermediate AC) using a procedure analogous to that of (1R,2S,3R,5S)-3-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(5-ethyl-tetrazol-2-yl)-cyclopentane-1,2-diol (Intermediate BA6) by replacing 5-ethyl-2H-tetrazole with 4-ethyl-2H-[1,2,3]triazole (first step a). MS (ES+) m/e 545.24 (MH+)

Sources & evidence

ORD record
ord-a98babf6d3e44f9fa30e2263d508fe59
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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