[(1S,2R,3S,4R)-4-(6-(2,2-Diphenyl-ethylamino)-2-{2-[3-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-ureido]-ethylcarbamoyl}-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-carbamic acid tert-butyl ester → 9-((1R,2S,3R,4S)-4-Amino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid {2-[3-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-ureido]-ethyl}-amide dihydrochloride

HRID 2382408Notes

Reaction equation

N[C@H]1C[C@@H](N2C=NC3C2=NC([Cl:33])=NC=3NCC(C2C=CC(O)=CC=2)C2C=CC(O)=CC=2)[C@H](O)[C@@H]1O.C(OC(=O)[NH:42][C@H:43]1[CH2:47][C@@H:46]([N:48]2[CH:56]=[N:55][C:54]3[C:49]2=[N:50][C:51]([C:72](=[O:92])[NH:73][CH2:74][CH2:75][NH:76][C:77]([NH:79][CH:80]2[CH2:85][CH2:84][N:83]([C:86]4[CH:91]=[CH:90][CH:89]=[CH:88][N:87]=4)[CH2:82][CH2:81]2)=[O:78])=[N:52][C:53]=3[NH:57][CH2:58][CH:59]([C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C@H:45]([OH:93])[C@@H:44]1[OH:94])(C)(C)C>>[ClH:33].[ClH:33].[N:83]1([C:86]2[CH:91]=[CH:90][CH:89]=[CH:88][N:87]=2)[CH2:84][CH2:85][CH:80]([NH:79][C:77](=[O:78])[NH:76][CH2:75][CH2:74][NH:73][C:72]([C:51]2[N:50]=[C:49]3[C:54]([N:55]=[CH:56][N:48]3[C@@H:46]3[CH2:47][C@H:43]([NH2:42])[C@@H:44]([OH:94])[C@H:45]3[OH:93])=[C:53]([NH:57][CH2:58][CH:59]([C:66]3[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=3)[C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=3)[N:52]=2)=[O:92])[CH2:81][CH2:82]1

Participants

Reactant 2

HCID 24863127[(1S,2R,3S,4R)-4-(6-(2,2-Diphenyl-ethylamino)-2-{2-[3-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-ureido]-ethylcarbamoyl}-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-carbamic acid tert-butyl ester

HCID 86647548(1S,2R,3S,5R)-3-Amino-5-{6-[2,2-bis-(4-hydroxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-cyclopentane-1,2-diol

Product 1

HCID 666311369-((1R,2S,3R,4S)-4-Amino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid {2-[3-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-ureido]-ethyl}-amide dihydrochloride

Procedure

The title compound is prepared analogously to (1S,2R,3S,5R)-3-Amino-5-{6-[2,2-bis-(4-hydroxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-cyclopentane-1,2-diol (example 7 step 2) by replacing N-((1S,2R,3S,4R)-4-{6-[2,2-Bis-(4-hydroxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide hydrochloride with (1S,2R,3S,4R)-4-(6-(2,2-Diphenyl-ethylamino)-2-{2-[3-(3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-ureido]-ethylcarbamoyl}-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-carbamic acid tert-butyl ester (Example 12).

Sources & evidence

ORD record: ord-aeb35c20fd264e97928cecad0876630a
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258141B2

Reaction notes

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