N-(2-Aminoethyl)piperidine → N-{(1S,2R,3S,4R)-2,3-Dihydroxy-4-[6-[(naphthalen-1-ylmethyl)-amino]-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-cyclopentyl}-propionamide trifluoroacetate

HRID 1697025Notes

Reaction equation

HRID 1697025 reaction equation
C1(C(C2C=CC=CC=2)CNC2N=C(N[C@H](CO)CC3C=CC=CC=3)N=[C:15]3[C:11]=2[N:12]=C[N:14]3[C@@H:30]2[CH2:34][C@H:33](NC(=O)CC)[C@@H:32](O)[C@H:31]2O)C=CC=CC=1.[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].Cl[C:56]1[N:64]=[C:63]2[C:59]([N:60]=[CH:61][N:62]2[C@@H:65]2[CH2:69][C@H:68]([NH:70][C:71](=[O:74])[CH2:72][CH3:73])[C@@H:67]([OH:75])[C@H:66]2[OH:76])=[C:58]([NH:77][CH2:78][C:79]2[C:88]3[C:83](=[CH:84][CH:85]=[CH:86][CH:87]=3)[CH:82]=[CH:81][CH:80]=2)[N:57]=1.N1(CCN)CCCCC1>>[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[OH:75][C@H:67]1[C@@H:66]([OH:76])[C@H:65]([N:62]2[CH:61]=[N:60][C:59]3[C:63]2=[N:64][C:56]([NH:12][CH2:11][CH2:15][N:14]2[CH2:30][CH2:34][CH2:33][CH2:32][CH2:31]2)=[N:57][C:58]=3[NH:77][CH2:78][C:79]2[C:88]3[C:83](=[CH:84][CH:85]=[CH:86][CH:87]=3)[CH:82]=[CH:81][CH:80]=2)[CH2:69][C@@H:68]1[NH:70][C:71](=[O:74])[CH2:72][CH3:73]

Participants

4

Reactant 3

HCID 33944N-(2-Aminoethyl)piperidineHCID 67019378N-{(1S,2R,3S,4R)-4-[6-(2,2-Diphenyl-ethylamino)-2-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamideHCID 86622652N-((1S,2R,3S,4R)-4-{2-chloro-6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate

Product 1

HCID 67019398N-{(1S,2R,3S,4R)-2,3-Dihydroxy-4-[6-[(naphthalen-1-ylmethyl)-amino]-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-cyclopentyl}-propionamide trifluoroacetate

Procedure

This compound is prepared analogously to N-{(1S,2R,3S,4R)-4-[6-(2,2-diphenyl-ethylamino)-2-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide (Example 16) by replacing N-{(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide (Example 4) with N-((1S,2R,3S,4R)-4-{2-chloro-6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate (Example 50) and by replacing (S)-2-amino-3-phenyl-propan-1-ol with 2-piperidin-1-yl-ethylamine.

Sources & evidence

ORD record
ord-b6a15308d43f46b8bddff4958266b129
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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