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

HRID 41503Notes

Reaction equation

HRID 41503 reaction equation
CS(C)=O.[P:5](=[O:9])([OH:8])([OH:7])[OH:6].[CH3:10][C:11]1[CH:19]=[C:18]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[C:38]4[C:33](=[CH:34][C:35]([O:41][CH3:42])=[C:36]([O:39][CH3:40])[CH:37]=4)[N:32]=[C:31]([NH:43][CH3:44])[N:30]=3)[CH:24]=2)=[O:21])[CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]>CC(O)C>[P:5]([OH:9])([OH:8])([OH:7])=[O:6].[CH3:10][C:11]1[CH:19]=[C:18]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[C:38]4[C:33](=[CH:34][C:35]([O:41][CH3:42])=[C:36]([O:39][CH3:40])[CH:37]=4)[N:32]=[C:31]([NH:43][CH3:44])[N:30]=3)[CH:24]=2)=[O:21])[CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 1004Phosphoric AcidHCID 66646296methyl N-[3-(6,7-dimethoxy-2-methylaminoquinazolin-4-yl)phenyl]terephthalamic acid

Product 1

HCID 68817101Methyl N-[3-(6,7-dimethoxy-2-methylaminoquinazolin-4-yl)phenyl]terephthalamic acid phosphate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Dimethyl sulfoxide (1 mL) and phosphoric acid (25 μL) were added to methyl N-[3-(6,7-dimethoxy-2-methylaminoquinazolin-4-yl)phenyl]terephthalamic acid (96.52 mg). Dimethyl sulfoxide (0.75 mL) was added to and dissolved in the mixture while heating the mixture, and then 2-propanol (2 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 (114.15 mg).

Workup

  1. dissolutiondissolved in the mixture
  2. temperaturewhile heating the mixture
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-61c35dd2450c4cffb9a1bf89dd25af39
Source dataset
uspto-grants-2013_09
Patent number
US08530654B2

Reaction notes

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