HCID 24755621, compound → HCID 25059377, compound

HRID 1929782Notes

Reaction equation

HRID 1929782 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])[C@@H:13]([OH:21])[C@H:12]2[OH:22])=[C:4]([NH:23][C@@H:24]2[CH2:28][CH2:27][N:26]([C:29]3[N:37]=[C:36]4[C:32]([N:33]=[CH:34][N:35]4[C@@H:38]4[CH2:42][C@H:41]([NH:43][C:44](=[O:47])[CH2:45][CH3:46])[C@@H:40]([OH:48])[C@H:39]4[OH:49])=[C:31]([NH:50][CH2:51][CH:52]([C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)[C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[N:30]=3)[CH2:25]2)[N:3]=1.[N:65]1[CH:70]=[CH:69][CH:68]=[C:67]([NH:71][C:72]([NH:74][C@@H:75]2[CH2:79][CH2:78][NH:77][CH2:76]2)=[O:73])[CH:66]=1>CCO>[N:65]1[CH:70]=[CH:69][CH:68]=[C:67]([NH:71][C:72](=[O:73])[NH:74][C@@H:75]2[CH2:79][CH2:78][N:77]([C:2]3[N:10]=[C:9]4[C:5]([N:6]=[CH:7][N:8]4[C@@H:11]4[CH2:15][C@H:14]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])[C@@H:13]([OH:21])[C@H:12]4[OH:22])=[C:4]([NH:23][C@@H:24]4[CH2:28][CH2:27][N:26]([C:29]5[N:37]=[C:36]6[C:32]([N:33]=[CH:34][N:35]6[C@@H:38]6[CH2:42][C@H:41]([NH:43][C:44](=[O:47])[CH2:45][CH3:46])[C@@H:40]([OH:48])[C@H:39]6[OH:49])=[C:31]([NH:50][CH2:51][CH:52]([C:53]6[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=6)[C:59]6[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=6)[N:30]=5)[CH2:25]4)[N:3]=3)[CH2:76]2)[CH:66]=1

Participants

4

Reactant 2

HCID 24755621HCID 24755621, compoundHCID 58025006HCID 58025006, compound

Product 1

HCID 25059377HCID 25059377, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-{(1S,2R,3S,4R)-4-[2-{(R)-3-[2-Chloro-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-6-ylamino]-pyrrolidin-1-yl}-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide (1 eq.) and 1-pyridin-3-yl-3-(R)-pyrrolidin-3-yl-urea (3 eq.) are dissolved in EtOH. The reaction mixture is refluxed at room temperature for 48 hours. The reaction mixture is reduced in vacuo and purified by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water-0.1% TFA) to yield the title compound.

Workup

  1. custompurified by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water-0.1% TFA)

Sources & evidence

ORD record
ord-79d97d9548a349ff8380b1755c7006bd
Source dataset
uspto-grants-2012_05
Patent number
US08188100B2

Reaction notes

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