1-(Pyridin-2-yl)piperidin-4-amine → N-{(1S,2R,3S,4R)-4-[6-(2,2-diphenyl-ethylamino)-2-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-ylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide trifluoroacetate

HRID 2382438Notes

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](=[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:101]2[CH:106]=[CH:105][CH:104]=[CH:103][N:102]=2)[CH2:99][CH2:98][CH:97]([NH2:100])[CH2:96][CH2:95]1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:82]1([CH:81]([C:88]2[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=2)[CH2:80][NH:79][C:60]2[N:59]=[C:58]([NH:100][CH:97]3[CH2:98][CH2:99][N:94]([C:101]4[CH:106]=[CH:105][CH:104]=[CH:103][N:102]=4)[CH2:95][CH2:96]3)[N:66]=[C:65]3[C:61]=2[N:62]=[CH:63][N:64]3[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])[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=1

Participants

Reactant 3

HCID 101979341-(Pyridin-2-yl)piperidin-4-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 86622630N-[(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl]-propionamide2×

Product 1

HCID 66631014N-{(1S,2R,3S,4R)-4-[6-(2,2-diphenyl-ethylamino)-2-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-ylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide 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 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 3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-ylamine. (MH+ 331.7)

Sources & evidence

ORD record: ord-668dc75169d24891bba6566eeda95693
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258141B2

Reaction notes

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