Hydrochloric Acid → HCID 42611021, compound

HRID 81667Notes

Reaction equation

HRID 81667 reaction equation
Cl([O-])=O.[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([O:31][CH2:32][CH:33]=[O:34])[CH:9]=[N:10][C:11]=1[O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][N:17]=[C:16]2[NH:23][C:24]1[CH:29]=[N:28][C:27]([CH3:30])=[CH:26][N:25]=1.CC(=CC)C.P([O-])(O)(O)=[O:41].[Na+].Cl>CC(O)(C)C.O>[Cl:5][C:6]1[CH:7]=[C:8]([O:31][CH2:32][C:33]([OH:41])=[O:34])[CH:9]=[N:10][C:11]=1[O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][N:17]=[C:16]2[NH:23][C:24]1[CH:29]=[N:28][C:27]([CH3:30])=[CH:26][N:25]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86645904{[5-Chloro-6-({4-[(5-methylpyrazin-2-yl)amino]quinazolin-6-yl}oxy)pyridin-3-yl]oxy}acetaldehyde

Product 1

HCID 42611021HCID 42611021, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

Sodium chlorite (30 mg, 0.33 mmol) was added to a water (0.3 ml)/2-methyl-2-propanol (1.2 ml) mixed solution of {[5-chloro-6-({4-[(5-methylpyrazin-2-yl)amino]quinazolin-6-yl}oxy)pyridin-3-yl]oxy}acetaldehyde (50 mg, 0.11 mmol) obtained in Example 32, 2-methyl-2-butene (0.051 ml, 0.48 mmol) and sodium dihydrogenphosphate (13 mg, 0.11 mmol), and the reaction solution was stirred at room temperature for 1 hour. Aqueous 1 N hydrochloric acid solution was added to the reaction solution, and extracted with chloroform/methanol (9:1). The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate to obtain the entitled compound (37 mg, yield: 77%) as a yellow solid.

Workup

  1. extractionextracted with chloroform/methanol (9:1)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8c001583026c4a42aaec16f3dcd80b71
Source dataset
uspto-grants-2014_09
Patent number
US08846700B2

Reaction notes

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