N-ethylhistamine → (1R,2S,3R,5S)-3-{6-(2,2-Diphenyl-ethylamino)-2-[2-(1-ethyl-1H-imidazol-4-yl)-ethylamino]-purin-9-yl}-5-(4-ethyl-[1,2,3]triazol-2-yl)-cyclopentane-1,2-diol trifluoroacetate

HRID 1641969Notes

Reaction equation

HRID 1641969 reaction equation
Cl[C:2]1N=C2C(N=CN2C2CC(N3C=C(CC)N=N3)C(O)C2O)=C(NCC(C2C=CC=CC=2)C2C=CC=CC=2)[N:3]=1.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[C:47]1([CH:53]([C:88]2[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=2)[CH2:54][NH:55][C:56]2[N:64]=[C:63]([NH:65]CCN3CCCCC3)[N:62]=[C:61]3[C:57]=2[N:58]=[CH:59][N:60]3[C@@H:74]2[CH2:78][C@H:77]([N:79]3[CH:83]=[C:82](CO)[CH:81]=[N:80]3)[C@@H:76]([OH:86])[C@H:75]2[OH:87])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.[CH2:94]([N:96]1[CH:100]=[C:99]([CH2:101][CH2:102]N)[N:98]=[CH:97]1)[CH3:95]>>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[C:88]1([CH:53]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:54][NH:55][C:56]2[N:64]=[C:63]([NH:65][CH2:102][CH2:101][C:99]3[N:98]=[CH:97][N:96]([CH2:94][CH3:95])[CH:100]=3)[N:62]=[C:61]3[C:57]=2[N:58]=[CH:59][N:60]3[C@@H:74]2[CH2:78][C@H:77]([N:79]3[N:80]=[C:81]([CH2:82][CH3:83])[CH:2]=[N:3]3)[C@@H:76]([OH:86])[C@H:75]2[OH:87])[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=1

Participants

4

Reactant 3

HCID 44292270N-ethylhistamineHCID 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 866228023-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-ethyl-[1,2,3]triazol-1-yl)-cyclopentane-1,2-diol

Product 1

HCID 66736596(1R,2S,3R,5S)-3-{6-(2,2-Diphenyl-ethylamino)-2-[2-(1-ethyl-1H-imidazol-4-yl)-ethylamino]-purin-9-yl}-5-(4-ethyl-[1,2,3]triazol-2-yl)-cyclopentane-1,2-diol trifluoroacetate

Procedure

This compound is prepared from 3-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-ethyl-[1,2,3]triazol-1-yl)-cyclopentane-1,2-diol (Intermediate BA9) 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 461 by replacing 1-(2-amino-ethyl)piperidine with 2-(1-ethyl-1H-imidazol-4-yl)-ethylamine (intermediate CD). MS (ES+) m/e 648.42 (MH+).

Sources & evidence

ORD record
ord-f9abdfdd61ea406c9c5b80370c99507c
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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