4-[3-(2-{[9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carbonyl]-amino}-ethyl)-ureido]-piperidine-1-carboxylic acid benzyl ester → 4-{[(R)-3-(3-{(R)-1-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-ureido)-pyrrolidine-1-carbonyl]-amino}-piperidine-1-carboxylic acid benzyl ester trifluoroacetate

HRID 1882607Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18](NCCNC(C2N=C3C(N=CN3[C@@H]3C[C@H](NC(=O)CC)[C@@H](O)[C@H]3O)=C(NCC(C3C=CC=CC=3)C3C=CC=CC=3)N=2)=O)=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:62][C:63]([F:68])([F:67])[C:64]([OH:66])=[O:65].[C:69]1([CH:75]([C:113]2[CH:118]=[CH:117][CH:116]=[CH:115][CH:114]=2)[CH2:76][NH:77][C:78]2[N:86]=[C:85]([N:87]3[CH2:91][CH2:90][C@@H:89]([NH:92][C:93]([NH:95][C@@H:96]4[CH2:100][CH2:99][NH:98][CH2:97]4)=[O:94])[CH2:88]3)[N:84]=[C:83]3[C:79]=2[N:80]=[CH:81][N:82]3[C@@H:101]2[CH2:105][C@H:104]([NH:106][C:107](=[O:110])[CH2:108][CH3:109])[C@@H:103]([OH:111])[C@H:102]2[OH:112])[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1>>[F:62][C:63]([F:68])([F:67])[C:64]([OH:66])=[O:65].[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([N:98]2[CH2:99][CH2:100][C@@H:96]([NH:95][C:93]([NH:92][C@@H:89]3[CH2:90][CH2:91][N:87]([C:85]4[N:84]=[C:83]5[C:79]([N:80]=[CH:81][N:82]5[C@@H:101]5[CH2:105][C@H:104]([NH:106][C:107](=[O:110])[CH2:108][CH3:109])[C@@H:103]([OH:111])[C@H:102]5[OH:112])=[C:78]([NH:77][CH2:76][CH:75]([C:113]5[CH:114]=[CH:115][CH:116]=[CH:117][CH:118]=5)[C:69]5[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=5)[N:86]=4)[CH2:88]3)=[O:94])[CH2:97]2)=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 666303744-[3-(2-{[9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carbonyl]-amino}-ethyl)-ureido]-piperidine-1-carboxylic acid benzyl ester

HCID 66630460N-((1S,2R,3S,4R)-4-{6-(2,2-Diphenyl-ethylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate

Product 1

HCID 866475634-{[(R)-3-(3-{(R)-1-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-ureido)-pyrrolidine-1-carbonyl]-amino}-piperidine-1-carboxylic acid benzyl ester trifluoroacetate

Procedure

The title compound is prepared analogously to 4-[3-(2-{[9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carbonyl]-amino}-ethyl)-ureido]-piperidine-1-carboxylic acid benzyl ester (Example 108) by replacing 9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid (2-amino-ethyl)-amide with N-((1S,2R,3S,4R)-4-{6-(2,2-diphenyl-ethylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate (Example 17 step 1). (MH+ 943.4)

Sources & evidence

ORD record: ord-c9f8e982a62d485c8e1293e9270102e0
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318750B2

Reaction notes

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