Hydrochloric Acid → HCID 53821205, compound

HRID 1023291Notes

Reaction equation

HRID 1023291 reaction equation
Cl.[C:2]1([C@H:8]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:24][CH2:25][CH2:26][O:27]C4CCCCO4)=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH3:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO>[C:2]1([C@H:8]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:24][CH2:25][CH2:26][OH:27])=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH3:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 54187764HCID 54187764, compound

Product 1

HCID 53821205HCID 53821205, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

120 ml of methanol and 2 ml of concentrated hydrochloric acid were given to 8.05 g of 4-[(R)-(1-Phenylethyl)amino]-7-[2-(tetrahydropyran-2-yloxy)ethoxy]-6-nitroquinazoline. After stirring for 1.5 hours at 50° C. the reaction mixture was neutralized with concentrated aqueous sodium carbonate solution and evaporated. The solid residue was dissolved in ethyl acetate and the obtained solution was washed with water, with concentrated aqueous sodium chloride solution, dried over magnesium sulfate solution and evaporated. The obtained yellow residue was stirred with 20 ml of tert-butyl methyl ether, suction filtered and dried in an exsiccator. Yield: 4.53 g (91% of theory); melting point: 192° C.-194° C.; mass spectrum (ESI−): m/z=353 [M−H]−.

Workup

  1. customevaporated
  2. dissolutionThe solid residue was dissolved in ethyl acetate
  3. washthe obtained solution was washed with water, with concentrated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate solution
  5. customevaporated
  6. stirringThe obtained yellow residue was stirred with 20 ml of tert-butyl methyl ether, suction
  7. filtrationfiltered
  8. customdried in an exsiccator

Sources & evidence

ORD record
ord-10d95d68fe494516a4a1eda7fd89374c
Source dataset
uspto-grants-2014_05
Patent number
US08722694B2

Reaction notes

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