(3R)-3-(Pyrrolidin-1-YL)pyrrolidine → HCID 66736567, compound

HRID 1641946Notes

Reaction equation

HRID 1641946 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=2)[CH2:9][NH:10][C:11]2[N:19]=[C:18]([Cl:20])[N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[C@@H:21]2[CH2:25][C@H:24]([N:26]3[N:30]=[N:29][C:28]([CH2:31][CH3:32])=[N:27]3)[C@@H:23]([OH:33])[C@H:22]2[OH:34])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C1(C(C2C=CC=CC=2)CN[C:58]2[N:66]=[C:65](NCCN3CCCCC3)N=[C:63]3[C:59]=2N=C[N:62]3[C@@H:76]2[CH2:80][C@H:79](N3C=C(CO)C=N3)[C@@H:78](O)[C@H]2O)C=CC=CC=1.N1([C@@H]2CCNC2)CCCC1>>[ClH:20].[N:62]1([C@@H:63]2[CH2:59][CH2:58][N:66]([C:18]3[N:17]=[C:16]4[C:12]([N:13]=[CH:14][N:15]4[C@@H:21]4[CH2:25][C@H:24]([N:26]5[N:30]=[N:29][C:28]([CH2:31][CH3:32])=[N:27]5)[C@@H:23]([OH:33])[C@H:22]4[OH:34])=[C:11]([NH:10][CH2:9][CH:8]([C:35]4[CH:36]=[CH:37][C:38]([OH:41])=[CH:39][CH:40]=4)[C:5]4[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=4)[N:19]=3)[CH2:65]2)[CH2:76][CH2:80][CH2:79][CH2:78]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 86622807(1R,2S,3R,5S)-3-{6-[2,2-Bis-(4-hydroxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-5-(5-ethyl-tetrazol-2-yl)-cyclopentane-1,2-diol

Product 1

HCID 66736567HCID 66736567, compound

Procedure

This compound is prepared from (1R,2S,3R,5S)-3-{6-[2,2-bis-(4-hydroxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-5-(5-ethyl-tetrazol-2-yl)-cyclopentane-1,2-diol (Intermediate BF1) 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 trifluoroacetate (Example 46) by replacing 1-(2-amino-ethyl)piperidine with (R)-[1,3′]bipyrrolidinyl (intermediate EB). MS (ES+) m/e 650.42 (MH+).

Sources & evidence

ORD record
ord-77c15308b8f2420ca7eb636c5c90627f
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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