N-(2-Aminoethyl)piperidine → N-{(1S,2R,3S,4R)-4-[6-(1-Ethyl-propylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

HRID 1696997Notes

Reaction equation

HRID 1696997 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:40]1[CH2:44][C@@H:43]([N:45]2[CH:53]=[N:52][C:51]3[C:46]2=NC(Cl)=NC=3Cl)C=[CH:41]1)C(=O)CC)(C)(C)C.NCCN1CCCCC1>>[CH2:25]([CH:24]([NH:23][C:4]1[N:3]=[C:2]([NH:52][CH2:51][CH2:46][N:45]2[CH2:53][CH2:41][CH2:40][CH2:44][CH2:43]2)[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[C@@H:11]1[CH2:15][C@H:14]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])[C@@H:13]([OH:21])[C@H:12]1[OH:22])[CH2:27][CH3:28])[CH3:26]

Participants

4

Reactant 3

HCID 33944N-(2-Aminoethyl)piperidineHCID 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 ester

Product 1

HCID 11547872N-{(1S,2R,3S,4R)-4-[6-(1-Ethyl-propylamino)-2-(2-piperidin-1-yl-ethylamino)-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 1-(2-aminoethyl)-piperidine to give the title compound using a procedure analogous to that of Example 9. MS (ES+) m/e 503 (MH+).

Sources & evidence

ORD record
ord-0936acb91db34b16b34da34afa69ea96
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

Loading…