4-Methylpyrazole → HCID 131729448, compound

HRID 1641890Notes

Reaction equation

HRID 1641890 reaction equation
ClC1N=C2C(N=CN2C2CC(N3C=C(C)C=N3)C([OH:22])C2O)=C(NCC(C2C=CC=CC=2)C2C=CC=CC=2)N=1.C(OC(=O)[O:43][C@H:44]1[CH2:48][C@@H:47]([N:49]2[CH:57]=[N:56][C:55]3[C:50]2=[N:51][C:52]([Cl:76])=[N:53][C:54]=3[NH:58][CH:59]([C:68]2[CH:73]=[CH:72][C:71]([O:74][CH3:75])=[CH:70][CH:69]=2)[C:60]2[CH:65]=[CH:64][C:63]([O:66][CH3:67])=[CH:62][CH:61]=2)[CH:46]=[CH:45]1)C.CC1C=NNC=1.[C:84]([SiH2:88][O:89][C:90]([C:102]1[CH:107]=[CH:106][CH:105]=[CH:104][CH:103]=1)([C:96]1[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=1)[C:91]1[CH:92]=[N:93][NH:94][CH:95]=1)([CH3:87])([CH3:86])[CH3:85]>>[CH3:75][O:74][C:71]1[CH:70]=[CH:69][C:68]([CH:59]([NH:58][C:54]2[N:53]=[C:52]([Cl:76])[N:51]=[C:50]3[C:55]=2[N:56]=[CH:57][N:49]3[C@@H:47]2[CH2:46][C@H:45]([N:94]3[CH:95]=[C:91]([C:90]([C:102]4[CH:107]=[CH:106][CH:105]=[CH:104][CH:103]=4)([C:96]4[CH:97]=[CH:98][CH:99]=[CH:100][CH:101]=4)[O:89][SiH2:88][C:84]([CH3:87])([CH3:85])[CH3:86])[CH:92]=[N:93]3)[C@@H:44]([OH:43])[C@H:48]2[OH:22])[C:60]2[CH:65]=[CH:64][C:63]([O:66][CH3:67])=[CH:62][CH:61]=2)=[CH:73][CH:72]=1

Participants

5

Reactant 4

HCID 34064-MethylpyrazoleHCID 86622620HCID 86622620, compoundHCID 86622805HCID 86622805, compoundHCID 131729449HCID 131729449, compound

Product 1

HCID 131729448HCID 131729448, compound

Procedure

The title compound is prepared by an analogous procedure to 1R,2S,3R,5S)-3-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-methyl-pyrazol-1-yl)-cyclopentane-1,2-diol (Intermediate BA1) by replacing Carbonic acid (1S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopent-2-enyl ester ethyl ester (Intermediate AA) in step 1 with Carbonic acid (1S,4R)-4-(6-{[bis-(4-methoxy-phenyl)-methyl]-amino}-2-chloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester (Intermediate AB) and by replacing 4-methylpyrazole with 4-(tert-Butyl-diphenyl-silanyloxymethyl)-1H-pyrazole. 1H nmr (CDCl3, 400 MHz); 7.70 (m, 4H), 7.50-7.20 (m, 13H), 6.85 (m, 4H), 6.60 (s, 1H), 5.60 (s, 1H), 4.80 (m, 1H), 4.70 (m, 4H), 4.30 (m, 1H), 3.80 (s, 6H), 3.00 (m, 1H), 2.70 (m, 1H), 1.10 (s, 9H).

Sources & evidence

ORD record
ord-0b5d9292482c425ba8df1c24461c46d7
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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