Dimethyl Sulfoxide → Methyl N-[3-(6,7-dimethoxy-2-methylaminoquinazolin-4-yl)phenyl]terephthalamic acid sulfate

HRID 41500Notes

Reaction equation

HRID 41500 reaction equation
CS(C)=O.[S:5](=[O:9])(=[O:8])([OH:7])[OH:6].CC(O)C.[CH3:14][C:15]1[CH:23]=[C:22]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]3[C:42]4[C:37](=[CH:38][C:39]([O:45][CH3:46])=[C:40]([O:43][CH3:44])[CH:41]=4)[N:36]=[C:35]([NH:47][CH3:48])[N:34]=3)[CH:28]=2)=[O:25])[CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18]>>[S:5]([OH:9])([OH:8])(=[O:7])=[O:6].[CH3:14][C:15]1[CH:23]=[C:22]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]3[C:42]4[C:37](=[CH:38][C:39]([O:45][CH3:46])=[C:40]([O:43][CH3:44])[CH:41]=4)[N:36]=[C:35]([NH:47][CH3:48])[N:34]=3)[CH:28]=2)=[O:25])[CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 66646296methyl N-[3-(6,7-dimethoxy-2-methylaminoquinazolin-4-yl)phenyl]terephthalamic acid

Product 1

HCID 68829027Methyl N-[3-(6,7-dimethoxy-2-methylaminoquinazolin-4-yl)phenyl]terephthalamic acid sulfate

Procedure

Dimethyl sulfoxide (1 mL) and sulfuric acid (26 μL) were added to and dissolved in methyl N-[3-(6,7-dimethoxy-2-methylaminoquinazolin-4-yl)phenyl]terephthalamic acid (103.92 mg) by heating. Then, 2-propanol (3 mL) was added to the mixture and the mixture was cooled to room temperature to be solidified. The solid was collected by filtration to yield the titled compound (112.12 mg).

Workup

  1. temperatureby heating
  2. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-9562c7bde316418084d6cd4b98abf39e
Source dataset
uspto-grants-2013_09
Patent number
US08530654B2

Reaction notes

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