(3R)-3-(Pyrrolidin-1-YL)pyrrolidine → (1R,2S,3R,5S)-3-[(R)-2-[1,3']Bipyrrolidinyl-1'-yl-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-ethyl-pyrazol-1-yl)-cyclopentane-1,2-diol Trifluoroacetate

HRID 1641961Notes

Reaction equation

HRID 1641961 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([N:16]3[CH:20]=[C:19]([CH2:21][CH3:22])[CH:18]=[N:17]3)[C@@H:13]([OH:23])[C@H:12]2[OH:24])=[C:4]([NH:25][CH2:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:3]=1.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].C1(C(C2C=CC=CC=2)CN[C:56]2[N:64]=[C:63](NCCN3CCCCC3)N=[C:61]3[C:57]=2N=C[N:60]3[C@@H:74]2[CH2:78][C@H:77](N3C=C(CO)C=N3)[C@@H:76](O)[C@H]2O)C=CC=CC=1.N1([C@@H]2CCNC2)CCCC1>>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[N:60]1([C@@H:61]2[CH2:57][CH2:56][N:64]([C:2]3[N:10]=[C:9]4[C:5]([N:6]=[CH:7][N:8]4[C@@H:11]4[CH2:15][C@H:14]([N:16]5[CH:20]=[C:19]([CH2:21][CH3:22])[CH:18]=[N:17]5)[C@@H:13]([OH:23])[C@H:12]4[OH:24])=[C:4]([NH:25][CH2:26][CH:27]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:3]=3)[CH2:63]2)[CH2:74][CH2:78][CH2:77][CH2:76]1

Participants

4

Reactant 3

HCID 7176272(3R)-3-(Pyrrolidin-1-YL)pyrrolidineHCID 66735860(1R,2S,3R,5S)-3-[6-(2,2-diphenyl-ethylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-5-(4-hydroxymethyl-pyrazol-1-yl)-cyclopentane-1,2-diol trifluoro-acetateHCID 86622836(1R,2S,3R,5S)-3-[2-Chloro 6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-ethyl-pyrazol-1-yl)-cyclopentane-1,2-diol

Product 1

HCID 66735787(1R,2S,3R,5S)-3-[(R)-2-[1,3']Bipyrrolidinyl-1'-yl-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-ethyl-pyrazol-1-yl)-cyclopentane-1,2-diol Trifluoroacetate

Procedure

This compound is prepared from (1R,2S,3R,5S)-3-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-ethyl-pyrazol-1-yl)-cyclopentane-1,2-diol (Intermediate BA8) using a procedure analogous to that of (1R,2S,3R,5S)-3-[6-(2,2-diphenyl-ethylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-5-(4-hydroxymethyl-pyrazol-1-yl)-cyclopentane-1,2-diol trifluoro-acetate (Example 461 by replacing 1-(2-amino-ethyl)piperidine with (R)-[1,3′]bipyrrolidinyl (intermediate EB). MS (ES+) m/e 648.44 (MH+).

Sources & evidence

ORD record
ord-5ea654bdb24346a099d042d6e3cb5a1e
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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