Hydrochloric Acid → HCID 136029925, compound

HRID 2079665Notes

Reaction equation

HRID 2079665 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[N:8][C:9]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([S:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)(=[O:22])=[O:21])=[CH:16][CH:15]=3)=[N:10]2)=[CH:5][CH:4]=1.C[S-].[Na+].Cl>CN1C(=O)CCC1.O>[O:26]1[CH2:27][CH2:28][N:23]([S:20]([C:17]2[CH:18]=[CH:19][C:14]([NH:13][C:9]3[N:8]=[CH:7][C:6]4[C:11](=[CH:12][C:3]([OH:2])=[CH:4][CH:5]=4)[N:10]=3)=[CH:15][CH:16]=2)(=[O:21])=[O:22])[CH2:24][CH2:25]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4378561Sodium methanethiolateHCID 671020437-methoxy-N-(4-(morpholinosulfonyl)phenyl)quinazolin-2-amine

Product 1

HCID 136029925HCID 136029925, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-methoxy-N-(4-(morpholinosulfonyl)phenyl)quinazolin-2-amine (1 eq) and sodium thiomethoxide (4 eq) in NMP was heated at 80° C. for 4 h. Reaction mixture was diluted with water and acidified with 1N HCl. Compound was extracted with ethyl acetate. The organic layer was washed with satd. NaHCO3, brine and dried over sodium sulfate. Filtration, evaporation and drying under vacuum provide 2-(4-(morpholinosulfonyl)phenylamino) quinazolin-7-ol as a light yellow viscous liquid in 99% yield. ES/MS m/z 387.0 (MH+).

Workup

  1. customReaction mixture
  2. extractionCompound was extracted with ethyl acetate
  3. washThe organic layer was washed with satd
  4. dry with materialNaHCO3, brine and dried over sodium sulfate
  5. filtrationFiltration, evaporation
  6. customdrying under vacuum

Sources & evidence

ORD record
ord-fad761c73a40434fbc03c5c1cff50de1
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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