(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 → HCID 86672498, compound

HRID 1896230Notes

Reaction equation

HRID 1896230 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][CH2:33][C:34]#[CH:35])[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:68]=[N:69][N:70]([C:72]4[CH:77]=[CH:76][C:75]([F:78])=[C:74]([N+:79]([O-:81])=[O:80])[CH:73]=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][CH2:33][C:34]3[N:68]=[N:69][N:70]([C:72]4[CH:77]=[CH:76][C:75]([F:78])=[C:74]([N+:79]([O-:81])=[O:80])[CH:73]=4)[CH:35]=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 86672499(1R,2R,3S,4R,5S)-4-(2-Chloro-6-(3-(nona-1,8-diynyl)benzylamino)-9H-purin-9-yl) bicyclo[3.1.0]hexane-2,3-diol

Product 1

HCID 86672498HCID 86672498, compoundYield 91%

Procedure

Compound 216 (91%) was synthesized from compound 213 following the same procedure as for compound 214. 1H NMR (CD3OD, 400 MHz) δ 8.56-8.54 (m, 1H), 8.40 (s, 1H), 8.13-8.18 (m, 2H), 7.60 (t, J=8.8 Hz, 1H), 7.37 (s, 1H), 7.30 (d, J=6.8 Hz, 1H), 7.24-7.21 (m, 2H), 4.79 (s, 1H), 4.72-4.69 (m, 3H), 3.90 (d, J=6.4 Hz, 1H), 2.84 (t, J=7.2 Hz, 2H), 2.45 (t, J=6.8 Hz, 2H), 2.01-1.95 (m, 1H), 1.86-1.79 (m, 2H), 1.68-1.58 (m, 5H), 1.33-1.30 (m, 1H), 0.82-0.72 (m, 1H). HRMS calculated for C33H32ClFN9O4 (M+H)+: 672.2250. Found 672.2245.

Sources & evidence

ORD record
ord-2ce9a787ff904915a24e5f6dc051cd22
Source dataset
uspto-grants-2013_08
Patent number
US08518957B2

Reaction notes

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