Phenyl pyridin-3-ylcarbamate → HCID 66630549, compound

HRID 2382473Notes

Reaction equation

HRID 2382473 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:15]=[C:14]3[C:10]([N:11]=[CH:12][N:13]3[C@@H:16]3[CH2:20][C@H:19]([NH:21][C:22](=[O:25])[CH2:23][OH:24])[C@@H:18]([OH:26])[C@H:17]3[OH:27])=[C:9]([NH:28][CH2:29][C:30]([C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=3)([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[OH:31])[N:8]=2)[CH2:3]1.C1([O:52][C:53](=O)[NH:54][C:55]2[CH:56]=[N:57][CH:58]=[CH:59][CH:60]=2)C=CC=CC=1>CN1C(=O)CCC1>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([C:30]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)([OH:31])[CH2:29][NH:28][C:9]2[N:8]=[C:7]([N:4]3[CH2:5][CH2:6][C@@H:2]([NH:1][C:53]([NH:54][C:55]4[CH:56]=[N:57][CH:58]=[CH:59][CH:60]=4)=[O:52])[CH2:3]3)[N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[C@@H:16]2[CH2:20][C@H:19]([NH:21][C:22](=[O:25])[CH2:23][OH:24])[C@@H:18]([OH:26])[C@H:17]2[OH:27])=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 6935890Phenyl pyridin-3-ylcarbamateHCID 66629757HCID 66629757, compound

Product 1

HCID 66630549HCID 66630549, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution comprising: N-((1S,2R,3S,4R)-4-{2-((R)-3-Amino-pyrrolidin-1-yl)-6-[2,2-bis-(4-chloro-phenyl)-2-hydroxy-ethylamino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-2-hydroxy-acetamide (Intermediate ZO; 1 equivalent) and pyridin-3-yl-carbamic acid phenyl ester (Intermediate ZB; 1 equivalent) in NMP is stirred at 100° C. for 1 hour. The solvent is removed in vacuo and the title compound is obtained after purification by column chromatography/crystallisation.

Workup

  1. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-e2b035fdf1904b86bd79f2a1ba3bd893
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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