Sodium Iodide → N-{(1S,2R,3S,4R)-4-[6-(2,2-Diphenyl-ethylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-N'-(2-piperidin-1-yl-ethyl)-oxalamide

HRID 1697009Notes

Reaction equation

HRID 1697009 reaction equation
ClC1N=C2[C:5]([N:6]=CN2)=[C:4]([NH:11][CH2:12][CH:13]([C:20]2[CH:25]=[CH:24]C=CC=2)C2C=CC=CC=2)N=1.Cl[C:27]1[N:35]=[C:34]2[C:30]([N:31]=[CH:32][N:33]2[C@@H:36]2[CH2:40][C@H:39]([NH:41][C:42]([C:44]3[O:48]N=CC=3)=[O:43])[C@@H:38]([OH:49])[C@H:37]2[OH:50])=[C:29]([NH:51][CH2:52][CH:53]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[N:28]=1.[NH2:66][CH2:67][CH2:68][N:69]1[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]1.[I-].[Na+]>>[C:60]1([CH:53]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH2:52][NH:51][C:29]2[N:28]=[C:27]([NH:66][CH2:67][CH2:68][N:69]3[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]3)[N:35]=[C:34]3[C:30]=2[N:31]=[CH:32][N:33]3[C@@H:36]2[CH2:40][C@H:39]([NH:41][C:42](=[O:43])[C:44]([NH:6][CH2:5][CH2:4][N:11]3[CH2:12][CH2:13][CH2:20][CH2:25][CH2:24]3)=[O:48])[C@@H:38]([OH:49])[C@H:37]2[OH:50])[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 33944N-(2-Aminoethyl)piperidineHCID 86622645Isoxazole-5-carboxylic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-amideHCID 178478404HCID 178478404, compound

Product 1

HCID 67019366N-{(1S,2R,3S,4R)-4-[6-(2,2-Diphenyl-ethylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-N'-(2-piperidin-1-yl-ethyl)-oxalamide

Procedure

The title compound is prepared using a method that is analogous to that used to prepare the compound of Example 22 using isoxazole-5-carboxylic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-amide, 1-(2-aminoethyl)-piperidine (51 mg, 0.4 mmol) and sodium iodide (6 mg, 0.04 mmol). LCMS (electrospray): m/z [MH+] 739.55

Sources & evidence

ORD record
ord-7dda6f6a942749f49b114704fe3a8ff7
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

Loading…