Maleic Acid → methyl (3-{[[3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)propyl](3-morpholin-4-ylpropyl)amino]methyl}phenyl)acetate dimaleate

HRID 1186254Notes

Reaction equation

[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[NH2:9][C:10]1[N:18]=[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])[N:16]=[C:15]2[C:11]=1[NH:12][C:13](=[O:49])[N:14]2[CH2:24][CH2:25][CH2:26][N:27]([CH2:37][C:38]1[CH:39]=[C:40]([CH2:44][C:45]([O:47][CH3:48])=[O:46])[CH:41]=[CH:42][CH:43]=1)[CH2:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>O1CCOCC1>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[NH2:9][C:10]1[N:18]=[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])[N:16]=[C:15]2[C:11]=1[NH:12][C:13](=[O:49])[N:14]2[CH2:24][CH2:25][CH2:26][N:27]([CH2:37][C:38]1[CH:39]=[C:40]([CH2:44][C:45]([O:47][CH3:48])=[O:46])[CH:41]=[CH:42][CH:43]=1)[CH2:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1

Participants

Conditions

Temperature: 40 °C

Procedure

A 27 mM solution of maleic acid in 1,4-dioxane (0.5 ml, 13.5 μmol) was added to a solution of methyl (3-{[[3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)propyl](3-morpholin-4-ylpropyl)amino]methyl}phenyl)acetate (4 mg, 7 μmol) in 1,4-dioxane (0.75 ml) at room temperature and the mixture was left standing overnight. The next day, the solution was heated to 40° C. and shaken for one hour, and thereafter allowed to cool to room temperature. The solvent was evaporated at room temperature to give methyl (3-{[[3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)propyl](3-morpholin-4-ylpropyl)amino]methyl}phenyl)acetate dimaleate as the final product.

Workup

waitthe mixture was left
temperatureto cool to room temperature
customThe solvent was evaporated at room temperature

Sources & evidence

ORD record: ord-83eb4ce9be7248c3aa3e926352162c01
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673907B2

Reaction notes

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