N-((1S,2R,3S,4R)-4-{6-(1-Ethyl-propylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate → N-((1S,2R,3S,4R)-4-{6-(3,3-Dimethyl-butylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate

HRID 1697023Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(C(NC1N=C([N:23]2[CH2:27][CH2:26][C@@H:25]([NH:28][C:29]([NH:31][C@@H:32]3[CH2:36][CH2:35][NH:34][CH2:33]3)=[O:30])[CH2:24]2)N=C2C=1N=CN2[C@@H]1C[C@H](NC(=O)CC)[C@@H](O)[C@H]1O)CC)C.FC(F)(F)C(O)=O.Cl[C:57]1[N:65]=[C:64]2[C:60]([N:61]=[CH:62][N:63]2[C@@H:66]2[CH2:70][C@H:69]([NH:71][C:72](=[O:75])[CH2:73][CH3:74])[C@@H:68]([OH:76])[C@H:67]2[OH:77])=[C:59]([NH:78][CH2:79][CH2:80][C:81]([CH3:84])([CH3:83])[CH3:82])[N:58]=1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:82][C:81]([CH3:84])([CH3:83])[CH2:80][CH2:79][NH:78][C:59]1[N:58]=[C:57]([N:23]2[CH2:27][CH2:26][C@@H:25]([NH:28][C:29]([NH:31][C@@H:32]3[CH2:36][CH2:35][NH:34][CH2:33]3)=[O:30])[CH2:24]2)[N:65]=[C:64]2[C:60]=1[N:61]=[CH:62][N:63]2[C@@H:66]1[CH2:70][C@H:69]([NH:71][C:72](=[O:75])[CH2:73][CH3:74])[C@@H:68]([OH:76])[C@H:67]1[OH:77]

Participants

Reactant 2

HCID 67019376N-((1S,2R,3S,4R)-4-{6-(1-Ethyl-propylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate

HCID 86622653N-{(1S,2R,3S,4R)-4-[2-chloro-6-(3,3-dimethyl-butylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide trifluoroacetate

Product 1

HCID 67274710N-((1S,2R,3S,4R)-4-{6-(3,3-Dimethyl-butylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate

Procedure

This compound is prepared analogously to N-((1S,2R,3S,4R)-4-{6-(1-ethyl-propylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate by replacing N-{(1S,2R,3S,4R)-4-[2-chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide with N-{(1S,2R,3S,4R)-4-[2-chloro-6-(3,3-dimethyl-butylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide trifluoroacetate.

Sources & evidence

ORD record: ord-b9a8345b11b04b34a1440c8e47ef3e4a
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163754B2

Reaction notes

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