(1R,2R,3S,4R,5S)-4-(2-Chloro-6-(3-(5-(1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)pent-1-ynyl)benzylamino)-9H-purin-9-yl)-bicyclo[3.1.0]hexane-2,3-diol → (1R,2R,3S,4R,5S)-4-(2-Chloro-6-(3-(6-(1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)hex-1-ynyl)benzylamino)-9H-purin-9-yl)-bicyclo[3.1.0]hexane-2,3-diol

HRID 1896229Notes

Reaction equation

HRID 1896229 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[C@@H:16]3[C@@H:14]([CH2:15]3)[C@@H:13]([OH:17])[C@H:12]2[OH:18])=[C:4]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[C:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]#[CH:34])[CH:22]=2)[N:3]=1.ClC1N=C2C(N=CN2[C@@H]2[C@@H]3[C@@H](C3)[C@@H](O)[C@H]2O)=C(NCC2C=CC=C(C#CCCCC3[N:67]=[N:68][N:69]([C:71]4[CH:76]=[CH:75][C:74]([F:77])=[C:73]([N+:78]([O-:80])=[O:79])[CH:72]=4)C=3)C=2)N=1>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[C@@H:16]3[C@@H:14]([CH2:15]3)[C@@H:13]([OH:17])[C@H:12]2[OH:18])=[C:4]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[C:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]3[N:67]=[N:68][N:69]([C:71]4[CH:76]=[CH:75][C:74]([F:77])=[C:73]([N+:78]([O-:80])=[O:79])[CH:72]=4)[CH:34]=3)[CH:22]=2)[N:3]=1

Participants

3

Reactant 2

HCID 86672494(1R,2R,3S,4R,5S)-4-(2-Chloro-6-(3-(5-(1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)pent-1-ynyl)benzylamino)-9H-purin-9-yl)-bicyclo[3.1.0]hexane-2,3-diolHCID 86672497(1R,2R,3S,4R,5S)-4-(2-Chloro-6-(3-(octa-1,7-diynyl)benzylamino)-9H-purin-9-yl) bicyclo[3.1.0]hexane-2,3-diol

Product 1

HCID 86672496(1R,2R,3S,4R,5S)-4-(2-Chloro-6-(3-(6-(1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)hex-1-ynyl)benzylamino)-9H-purin-9-yl)-bicyclo[3.1.0]hexane-2,3-diolYield 95%

Procedure

Compound 215 (95%) was synthesized from compound 212 following the same procedure as for compound 214. 1H NMR (CDCl3, 400 MHz) δ 8.44-8.39 (m, 1H), 8.07-8.11 (m, 1H), 7.83 (s, 1H), 7.77 (s, 1H), 7.51-7.43 (m, 2H), 7.33-7.26 (m, 3H), 6.58 (br s, 1H), 4.87 (s, 1H), 4.79 (br s, 2H), 4.15 (s, 1H), 4.02 (d, J=6.8 Hz, 1H), 2.89 (t, J=7.6 Hz, 2H), 2.49 (t, J=6.8 Hz, 2H), 2.08-2.04 (m, 1H), 1.96-1.90 (m, 2H), 1.76-1.64 (m, 3H), 1.31-1.28 (m, 1H), 0.79-0.85 (m, 1H). HRMS calculated for C32H30ClFN9O4 (M+H)+: 658.2093. Found 658.2124.

Sources & evidence

ORD record
ord-ab59c6b1180f4f8ca8e3b6a3faf3d79d
Source dataset
uspto-grants-2013_08
Patent number
US08518957B2

Reaction notes

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