N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide → N-{(1S,2R,3S,4R)-4-[2-(4-Amino-cyclohexylamino)-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

HRID 1696998Notes

Reaction equation

HRID 1696998 reaction equation
Cl[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:17](=[O:20])[CH2:18][CH3:19])[C@@H:13]([OH:21])[C@H:12]2[OH:22])=[C:4]([NH:23][CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[N:3]=1.C(OC(=O)N([C@H]1C[C@@H](N2C=NC3C2=NC(Cl)=NC=3Cl)C=C1)C(=O)CC)(C)(C)C.[NH2:57][C@H:58]1[CH2:63][CH2:62][C@H:61]([NH2:64])[CH2:60][CH2:59]1>>[NH2:57][CH:58]1[CH2:63][CH2:62][CH:61]([NH:64][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[C@@H:11]3[CH2:15][C@H:14]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])[C@@H:13]([OH:21])[C@H:12]3[OH:22])=[C:4]([NH:23][CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[N:3]=2)[CH2:60][CH2:59]1

Participants

4

Reactant 3

HCID 11647233N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamideHCID 86622633[(1S,4R)-4-(2,6-Dichloro-purin-9-yl)-cyclopent-2-enyl]-propionyl-carbamic acid tert-butyl esterHCID 178511674HCID 178511674, compound

Product 1

HCID 11554921N-{(1S,2R,3S,4R)-4-[2-(4-Amino-cyclohexylamino)-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

Procedure

N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide (the compound of Example 14) is reacted with trans-1,4-diaminocyclohexane to give the title compound using a procedure analogous to that of Example 9. MS (ES+) m/e 489 (MH+).

Sources & evidence

ORD record
ord-833eb7f68c7f4555a6aeb2d2cc9e9b9c
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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