Phenyl pyridin-3-ylcarbamate → HCID 66630901, compound

HRID 2382470Notes

Reaction equation

HRID 2382470 reaction equation
[CH2:1]([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)[C:2]1C=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](OCC4C=CC=CC=4)C)[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[C:117](=[O:127])[NH:118][CH2:119][C:120]2[CH:125]=[CH:124][CH:123]=[C:122]([OH:126])[CH:121]=2)C=CC=CC=1.C1(OC(=O)NC2C=NC=CC=2)C=CC=CC=1>>[C:98]1([CH:97]([C:104]2[CH:105]=[CH:106][CH:107]=[CH:108][CH:109]=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][CH2:119][C:120]4[CH:125]=[CH:124][CH:123]=[C:122]([OH:126])[CH:121]=4)=[O:127])[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])[CH2:2][CH2:1][OH:8])[C@@H:77]([OH:93])[C@H:76]2[OH:94])[CH:99]=[CH:100][CH:101]=[CH:102][CH:103]=1

Participants

5

Reactant 4

HCID 6935890Phenyl pyridin-3-ylcarbamateHCID 44185157HCID 44185157, compoundHCID 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 66630901HCID 66630901, 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)-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-benzyloxy-propionamide (Example 181, step 4) and (3-Hydroxy-benzyl)-carbamic acid phenyl ester (Intermediate ZD) for pyridin-3-yl-carbamic acid phenyl ester (Intermediate ZB).

Sources & evidence

ORD record
ord-25cb01a8f1544615896e32eb4a022a68
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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