Phenyl pyridin-3-ylcarbamate → HCID 66631344, compound

HRID 2382472Notes

Reaction equation

HRID 2382472 reaction equation
C([O:8][C@H](C)C(N[C@H]1C[C@@H](N2C=NC3C2=NC(N2CC[C@@H](NC(NC4C=NC=CC=4)=O)C2)=NC=3NCC(C2C=CC=CC=2)C2C=CC=CC=2)[C@H](O)[C@@H]1O)=O)C1C=CC=CC=1.[NH2:60][C@@H:61]1[CH2:65][CH2:64][N:63]([C:66]2[N:74]=[C:73]3[C:69]([N:70]=[CH:71][N:72]3[C@@H:75]3[CH2:79][C@H:78]([NH:80][C:81](=[O:92])[C@H:82](OCC4C=CC=CC=4)[CH3:83])[C@@H:77]([OH:93])[C@H:76]3[OH:94])=[C:68]([NH:95][CH2:96][CH:97]([C:104]3[CH:109]=[CH:108][CH:107]=[CH:106][CH:105]=3)[C:98]3[CH:103]=[CH:102][CH:101]=[CH:100][CH:99]=3)[N:67]=2)[CH2:62]1.C1([O:116][C:117](=O)[NH:118][C:119]2[CH:124]=[CH:123][CH:122]=[C:121]([S:125](=[O:128])(=[O:127])[NH2:126])[CH:120]=2)C=CC=CC=1.C1(OC(=O)NC2C=NC=CC=2)C=CC=CC=1>>[C:104]1([CH:97]([C:98]2[CH:99]=[CH:100][CH:101]=[CH:102][CH:103]=2)[CH2:96][NH:95][C:68]2[N:67]=[C:66]([N:63]3[CH2:64][CH2:65][C@@H:61]([NH:60][C:117]([NH:118][C:119]4[CH:124]=[CH:123][CH:122]=[C:121]([S:125](=[O:127])(=[O:128])[NH2:126])[CH:120]=4)=[O:116])[CH2:62]3)[N:74]=[C:73]3[C:69]=2[N:70]=[CH:71][N:72]3[C@@H:75]2[CH2:79][C@H:78]([NH:80][C:81](=[O:92])[CH2:82][CH2:83][OH:8])[C@@H:77]([OH:93])[C@H:76]2[OH:94])[CH:105]=[CH:106][CH:107]=[CH:108][CH:109]=1

Participants

5

Reactant 4

HCID 6935890Phenyl pyridin-3-ylcarbamateHCID 39870106129513-94-6HCID 66630466(R)-N-{(1S,2R,3S,4R)-4-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-benzyloxy-propionamideHCID 66630596HCID 66630596, compound

Product 1

HCID 66631344HCID 66631344, compound

Procedure

The title compound was prepared analogously to (R)-2-benzyloxy-N-((1S,2R,3S,4R)-4-{6-(2,2-diphenyl-ethylamino)-2-[(R)-3-(3-pyridin-3-yl-ureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide (Example 181, step 5), by substituting N-{(1S,2R,3S,4R)-4-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-3-hydroxy-propionamide (Intermediate ZG) for (R)—N-{(1S,2R,3S,4R)-4-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-benzyloxy-propionamide (Example 181, step 4) and (3-Sulfamoyl-phenyl)-carbamic acid phenyl ester (Intermediate ZF) for pyridin-3-yl-carbamic acid phenyl ester (Intermediate ZB).

Sources & evidence

ORD record
ord-ae3c9e9664014ea6b612b5d072189ca0
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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