Phenyl pyridin-3-ylcarbamate → HCID 66630596, compound

HRID 2382463Notes

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:33])[C@H:23]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH3:24])[C@@H:18]([OH:34])[C@H:17]3[OH:35])=[C:9]([NH:36][CH2:37][CH:38]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:8]=2)[CH2:3]1.C1([O:57][C:58](=O)[NH:59][C:60]2[CH:61]=[N:62][CH:63]=[CH:64][CH:65]=2)C=CC=CC=1>CN1C(=O)CCC1>[CH2:26]([O:25][C@H:23]([CH3:24])[C:22]([NH:21][C@H:19]1[CH2:20][C@@H:16]([N:13]2[CH:12]=[N:11][C:10]3[C:14]2=[N:15][C:7]([N:4]2[CH2:5][CH2:6][C@@H:2]([NH:1][C:58]([NH:59][C:60]4[CH:61]=[N:62][CH:63]=[CH:64][CH:65]=4)=[O:57])[CH2:3]2)=[N:8][C:9]=3[NH:36][CH2:37][CH:38]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[C@H:17]([OH:35])[C@@H:18]1[OH:34])=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution comprising (R)—N-{(1S,2R,3S,4R)-4-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-benzyloxy-propionamide (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

customThe solvent is removed in vacuo

Sources & evidence

ORD record: ord-877fe4f47827474ba8ec6672305bc95d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258141B2

Reaction notes

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