(3R)-1-benzylpyrrolidin-3-amine → cyclobutanecarboxylic acid {(1S,2R,3S,4R)-4-[2-((R)-1-benzyl-pyrrolidin-3-ylamino)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-amide trifluoroacetate

HRID 1882585Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].N[C@@H]1CCN(C2N=C3C(N=CN3[C@@H]3C[C@H](NC(=O)COCC4C=CC=CC=4)[C@@H](O)[C@H]3O)=C(NCC(C3C=CC=CC=3)C3C=CC=CC=3)N=2)C1.Cl[C:58]1[N:66]=[C:65]2[C:61]([N:62]=[CH:63][N:64]2[C@@H:67]2[CH2:71][C@H:70]([NH:72][C:73]([CH:75]3[CH2:78][CH2:77][CH2:76]3)=[O:74])[C@@H:69]([OH:79])[C@H:68]2[OH:80])=[C:60]([NH:81][CH2:82][CH:83]([C:90]2[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=2)[C:84]2[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=2)[N:59]=1.[CH2:96]([N:103]1[CH2:107][CH2:106][C@@H:105]([NH2:108])[CH2:104]1)[C:97]1[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:96]([N:103]1[CH2:107][CH2:106][C@@H:105]([NH:108][C:58]2[N:66]=[C:65]3[C:61]([N:62]=[CH:63][N:64]3[C@@H:67]3[CH2:71][C@H:70]([NH:72][C:73]([CH:75]4[CH2:78][CH2:77][CH2:76]4)=[O:74])[C@@H:69]([OH:79])[C@H:68]3[OH:80])=[C:60]([NH:81][CH2:82][CH:83]([C:84]3[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=3)[C:90]3[CH:91]=[CH:92][CH:93]=[CH:94][CH:95]=3)[N:59]=2)[CH2:104]1)[C:97]1[CH:98]=[CH:99][CH:100]=[CH:101][CH:102]=1

Participants

Reactant 3

HCID 1519354(3R)-1-benzylpyrrolidin-3-amine

HCID 66630722N-{(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-acetamide trifluoroacetate

HCID 86622641Cyclobutanecarboxylic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-amide2×

Product 1

HCID 86635833cyclobutanecarboxylic acid {(1S,2R,3S,4R)-4-[2-((R)-1-benzyl-pyrrolidin-3-ylamino)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-amide trifluoroacetate

Procedure

This compound is prepared analogously to 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-acetamide trifluoroacetate Example 1 (Step 2) by replacing 2-benzyloxy-N-{(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-acetamide with cyclobutanecarboxylic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-amide (Intermediate K) and by replacing (3R)-3-aminopyrrolidine with (R)-1-benzyl-pyrrolidin-3-ylamine. (MH+ 687.5)

Sources & evidence

ORD record: ord-299c95dc594c474e856710c3e948a91b
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318750B2

Reaction notes

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