CID 24193465 → N-{(1S,2R,3S,4R)-4-[6-(2,2-diphenyl-ethylamino)-2-(4-nitro-pyrazol-1-yl)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide

HRID 1882547Notes

Reaction equation

HRID 1882547 reaction equation
C(OC(C1C=NN(C2N=C3C(N=CN3[C@@H]3C[C@H](NC(=O)CC)[C@@H](O)[C@H]3O)=C(NC(C3C=CC(OC)=CC=3)C3C=CC(OC)=CC=3)N=2)C=1)=O)C.[C:50]1([CH:56]([C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=2)[CH2:57][NH:58][C:59]2[N:67]=[C:66]([NH:68][NH2:69])[N:65]=[C:64]3[C:60]=2[N:61]=[CH:62][N:63]3[C@@H:70]2[CH2:74][C@H:73]([NH:75][C:76](=[O:79])[CH2:77][OH:78])[C@@H:72]([OH:80])[C@H:71]2[OH:81])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.[N+:88]([CH:91]([CH:94]=O)[CH:92]=O)([O-:90])=[O:89].[Na]>>[C:82]1([CH:56]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH2:57][NH:58][C:59]2[N:67]=[C:66]([N:68]3[CH:94]=[C:91]([N+:88]([O-:90])=[O:89])[CH:92]=[N:69]3)[N:65]=[C:64]3[C:60]=2[N:61]=[CH:62][N:63]3[C@@H:70]2[CH2:74][C@H:73]([NH:75][C:76](=[O:79])[CH2:77][OH:78])[C@@H:72]([OH:80])[C@H:71]2[OH:81])[CH:83]=[CH:84][CH:85]=[CH:86][CH:87]=1

Participants

4

Reactant 3

HCID 24193465CID 24193465HCID 66630575N-{(1S,2R,3S,4R)-4-[6-(2,2-diphenyl-ethylamino)-2-hydrazino-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamideHCID 666310101-[6-{[bis-(4-methoxy-phenyl)-methyl]-amino}-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 66630082N-{(1S,2R,3S,4R)-4-[6-(2,2-diphenyl-ethylamino)-2-(4-nitro-pyrazol-1-yl)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide

Procedure

The title compound is prepared analogously to 1-[6-{[bis-(4-methoxy-phenyl)-methyl]-amino}-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (example 168, step 3), by reaction of N-{(1S,2R,3S,4R)-4-[6-(2,2-diphenyl-ethylamino)-2-hydrazino-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide (Intermediate ZP1) and sodium nitromalonaldehyde (prepared as described by Fanta P. E. Org. Syntheses, Coll. Vol. 4 (1963), pp 844-845).

Sources & evidence

ORD record
ord-3dbc7e35bbf9402abf04e7b83ad8acbd
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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