(3R)-3-(Pyrrolidin-1-YL)pyrrolidine → N-{(1S,2R,3S,4R)-4-[(R)-2-[1,3']Bipyrrolidinyl-1'-yl-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide hydrochloride

HRID 2382447Notes

Reaction equation

HRID 2382447 reaction equation
FC(F)(F)C(O)=O.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:57][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](=[O:76])[CH2:74][CH3:75])[C@@H:69]([OH:77])[C@H:68]2[OH:78])=[C:60]([NH:79][CH2:80][CH:81]([C:88]2[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=2)[C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=2)[N:59]=1.[N:94]1([C@@H:99]2[CH2:103][CH2:102][NH:101][CH2:100]2)[CH2:98][CH2:97][CH2:96][CH2:95]1>>[ClH:57].[N:94]1([C@@H:99]2[CH2:103][CH2:102][N:101]([C:58]3[N:66]=[C:65]4[C:61]([N:62]=[CH:63][N:64]4[C@@H:67]4[CH2:71][C@H:70]([NH:72][C:73](=[O:76])[CH2:74][CH3:75])[C@@H:69]([OH:77])[C@H:68]4[OH:78])=[C:60]([NH:79][CH2:80][CH:81]([C:82]4[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=4)[C:88]4[CH:89]=[CH:90][CH:91]=[CH:92][CH:93]=4)[N:59]=3)[CH2:100]2)[CH2:98][CH2:97][CH2:96][CH2:95]1

Participants

4

Reactant 3

HCID 7176272(3R)-3-(Pyrrolidin-1-YL)pyrrolidine2×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 trifluoroacetateHCID 86622630N-[(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl]-propionamide2×

Product 1

HCID 66630578N-{(1S,2R,3S,4R)-4-[(R)-2-[1,3']Bipyrrolidinyl-1'-yl-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide hydrochloride

Procedure

The title 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 N-{(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide (Intermediate J) and by replacing (3R)-3-aminopyrrolidine with (R)-[1,3′]bipyrrolidinyl (Intermediate N). (MH+ 625.4)

Sources & evidence

ORD record
ord-c31b12d128ae4ed5a3c153924475a76a
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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