(1R,2S,3R,5S)-3-(2,6-Dichloro-purin-9-yl)-5-(4-hydroxymethyl-[1,2,3]triazol-2-yl)-cyclopentane-1,2-diol → (1R,2S,3R,5S)-3-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-hydroxymethyl-[1,2,3]triazol-2-yl)-cyclopentane-1,2-diol

HRID 215862Notes

Reaction equation

HRID 215862 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([NH:16]C(=O)CC)[C@@H:13]([OH:21])[C@H:12]2[OH:22])=[C:4]([NH:23][CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:3]=1.ClC1N=C2C(N=CN2[C@@H]2C[C@H](NC(=O)CC)[C@@H](O)[C@H]2O)=C(Cl)N=1.ClC1N=C2C(N=CN2[C@@H]2C[C@H](N3[N:80]=[C:79]([CH2:81][OH:82])[CH:78]=[N:77]3)[C@@H](O)[C@H]2O)=C(Cl)N=1>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([N:16]3[N:80]=[C:79]([CH2:81][OH:82])[CH:78]=[N:77]3)[C@@H:13]([OH:21])[C@H:12]2[OH:22])=[C:4]([NH:23][CH2:24][CH:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:3]=1

Participants

4

Reactant 3

HCID 59418979(1R,2S,3R,5S)-3-(2,6-Dichloro-purin-9-yl)-5-(4-hydroxymethyl-[1,2,3]triazol-2-yl)-cyclopentane-1,2-diolHCID 86622629N-[(1S,2R,3S,4R)-4-(2,6-Dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamideHCID 86622630N-[(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl]-propionamide

Product 1

HCID 59496934(1R,2S,3R,5S)-3-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-hydroxymethyl-[1,2,3]triazol-2-yl)-cyclopentane-1,2-diol

Procedure

(1R,2S,3R,5S)-3-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-hydroxymethyl-[1,2,3]triazol-2-yl)-cyclopentane-1,2-diol is prepared analogously to N-{(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide by replacing N-[(1S,2R,3S,4R)-4-(2,6-dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide, with (1R,2S,3R,5S)-3-(2,6-dichloro-purin-9-yl)-5-(4-hydroxymethyl-[1,2,3]triazol-2-yl)-cyclopentane-1,2-diol (Intermediate FC).

Sources & evidence

ORD record
ord-34db5456965944eca467d0b2e13a03a1
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

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