Hydrochloric Acid → HCID 52932914, compound

HRID 536076Notes

Reaction equation

HRID 536076 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([NH:16][C:17]3[CH:18]=[C:19]([S:29]([NH:32][CH3:33])(=[O:31])=[O:30])[CH:20]=[CH:21][C:22]=3[O:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[N:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1.[CH3:34][O-:35].[Na+].Cl>CO.C([O-])(O)=O.[Na+]>[CH3:33][NH:32][S:29]([C:19]1[CH:20]=[CH:21][C:22]([O:23][CH2:24][C:25]([F:26])([F:27])[F:28])=[C:17]([NH:16][C:10]2[C:9]3[C:14](=[CH:15][C:6]([O:5][CH2:4][CH2:3][CH2:2][O:35][CH3:34])=[CH:7][CH:8]=3)[N:13]=[CH:12][N:11]=2)[CH:18]=1)(=[O:30])=[O:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 52935241HCID 52935241, compound

Product 1

HCID 52932914HCID 52932914, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 3-({7-[(3-chloropropyl)oxy]-4-quinazolinyl}amino)-N-methyl-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide (150 mg, 0.297 mmol) in MeOH (3 mL) was treated with a solution of 25% sodium methoxide in methanol (3 g, 13.88 mmol) and subjected to microwave irradiation (100° C.) for 10 minutes before being cooled and neutralized with the addition of concentrated HCl. The resulting solution was diluted with saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic extracts were dried (sodium sulfate), concentrated, and subjected to reverse phase HPLC (30-70% MeCN/aq. NH4OH pH 10, XBridge C18 OBD 30×150 mm, 5 μm) to give N-methyl-3-[(7-{[3-(methyloxy)propyl]oxy}-4-quinazolinyl)amino]-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide (37 mg, 25%) as a white solid.

Workup

  1. customsubjected to microwave irradiation (100° C.) for 10 minutes
  2. temperaturebefore being cooled
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic extracts were dried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-43d190ac6f13404e92367ec4c8e537c8
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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