1H-Indole-4-boronic acid → 2-(9-(2-hydroxyethyl)-2-(1H-indol-4-yl)-6-morpholino-9H-purin-8-yl)propan-2-ol

HRID 2093386Notes

Reaction equation

HRID 2093386 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[C:15]([C:16]([OH:19])([CH3:18])[CH3:17])=[N:14][C:13]2[C:8]1=[N:9][C:10](Cl)=[N:11][C:12]=2[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)(=O)C.[NH:27]1[C:35]2[CH:34]=[CH:33][CH:32]=[C:31](B(O)O)[C:30]=2[CH:29]=[CH:28]1>>[OH:4][CH2:5][CH2:6][N:7]1[C:15]([C:16]([OH:19])([CH3:18])[CH3:17])=[N:14][C:13]2[C:8]1=[N:9][C:10]([C:31]1[CH:32]=[CH:33][CH:34]=[C:35]3[C:30]=1[CH:29]=[CH:28][NH:27]3)=[N:11][C:12]=2[N:20]1[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 27631731H-Indole-4-boronic acidHCID 580152242-(2-Chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)ethyl acetate

Product 1

HCID 444774282-(9-(2-hydroxyethyl)-2-(1H-indol-4-yl)-6-morpholino-9H-purin-8-yl)propan-2-ol

Procedure

2-(2-Chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)ethyl acetate (165 mg) was treated with indole-4-boronic acid via General Procedure A and purified via reverse phase HPLC to give 21 mg of 101 as a white solid. MS (Q1) 423.2 (M)+

Workup

  1. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-abcd5c18543547559d0e6261c8eb35a5
Source dataset
uspto-grants-2013_05
Patent number
US08445487B2

Reaction notes

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