Propionamide → N-[(R)-1-[6-[2,2-Bis-(4-methoxy-phenyl)-ethylamino]-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-pyrrolidin-3-yl}-isonicotinamide hydrochloride

HRID 2382443Notes

Reaction equation

HRID 2382443 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.N[C@@H:9]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.[NH:57]1[CH2:61][CH2:60][C@@H:59]([NH:62][C:63](=[O:70])[C:64]2[CH:69]=[CH:68][N:67]=[CH:66][CH:65]=2)[CH2:58]1.[CH3:71][O:72][C:73]1[CH:78]=[CH:77][C:76]([CH:79]([C:104]2[CH:109]=CC(OC)=[CH:106][CH:105]=2)[CH2:80][NH:81][C:82]2[N:90]=[C:89]([Cl:91])[N:88]=[C:87]3[C:83]=2[N:84]=[CH:85][N:86]3[C@@H:92]2[CH2:96][C@H:95]([NH:97][C:98](=[O:101])[CH2:99][CH3:100])[C@@H:94]([OH:102])[C@H:93]2[OH:103])=[CH:75][CH:74]=1.C(OC(=O)N([C@H]1C[C@@H](N2C=NC3C2=NC(Cl)=NC=3Cl)[C@H](O)[C@@H]1O)C(=O)CC)(C)(C)C.C(N)(=O)CC>>[ClH:91].[CH3:71][O:72][C:73]1[CH:78]=[CH:77][C:76]([CH:79]([C:104]2[CH:109]=[CH:2][C:3]([O:5][CH3:9])=[CH:106][CH:105]=2)[CH2:80][NH:81][C:82]2[N:90]=[C:89]([N:57]3[CH2:61][CH2:60][C@@H:59]([NH:62][C:63](=[O:70])[C:64]4[CH:69]=[CH:68][N:67]=[CH:66][CH:65]=4)[CH2:58]3)[N:88]=[C:87]3[C:83]=2[N:84]=[CH:85][N:86]3[C@@H:92]2[CH2:96][C@H:95]([NH:97][C:98](=[O:101])[CH2:99][CH3:100])[C@@H:94]([OH:102])[C@H:93]2[OH:103])=[CH:75][CH:74]=1

Participants

6

Reactant 5

HCID 6578PropionamideHCID 44140426[(1S,2R,3S,4R)-4-(2,6-dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionyl-carbamic acid tert-butyl ester2×HCID 66630437(R)-N-Pyrrolidin-3-yl-isonicotinamide2×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 86647562N-((1S,2R,3S,4R)-4-{6-[2,2-Bis-(4-methoxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide

Product 1

HCID 66630542N-[(R)-1-[6-[2,2-Bis-(4-methoxy-phenyl)-ethylamino]-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-pyrrolidin-3-yl}-isonicotinamide hydrochloride

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 (3R)-3-aminopyrrolidine with (R)—N-pyrrolidin-3-yl-isonicotinamide (Intermediate O) and 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-{6-[2,2-Bis-(4-methoxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide {prepared from [(1S,2R,3S,4R)-4-(2,6-dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionyl-carbamic acid tert-butyl ester (Intermediate G) and the appropriate amine using a procedure analogous to 2R,3S,4R)-4-{6-[2,2-Bis-(4-hydroxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide (Example 22 steps 1 and 2)}. (MH+ 736.5)

Sources & evidence

ORD record
ord-3d6deb56f7b3401caf0a55e66f976d0e
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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