Hydrochloric Acid → N-(3-Chloro-4-fluorophenyl)-7-(3-morpholinopropoxy)-6-nitroquinazolin-4-amine

HRID 2205319Notes

Reaction equation

HRID 2205319 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1F)[N:10]=[CH:9][N:8]=[C:7]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([Cl:23])[CH:17]=1)([O-:3])=[O:2].[N:24]1([CH2:30][CH2:31][CH2:32][OH:33])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.CC(C)([O-])C.[K+].Cl>CS(C)=O.O>[Cl:23][C:18]1[CH:17]=[C:16]([NH:15][C:7]2[C:6]3[C:11](=[CH:12][C:13]([O:33][CH2:32][CH2:31][CH2:30][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[N:10]=[CH:9][N:8]=2)[CH:21]=[CH:20][C:19]=1[F:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1995763-Morpholino-1-propanolHCID 10640649N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitroquinazolin-4-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 10600107N-(3-Chloro-4-fluorophenyl)-7-(3-morpholinopropoxy)-6-nitroquinazolin-4-amineYield 90%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

6-nitro-4-(3-chloro-4-fluorophenylamino)-7-fluoro-quinazoline (1 eq.) and morpholine-propanol (1.5 eq.) were dissolved in DMSO (10 ml), the solution was stirred for 5 mins with a water bath. A solution of potassium tert-butoxide (3.0 eq.) in DMSO (5 ml) was added slowly to the solution mentioned-above in drops, the mixture was stirred at room temperature for further 30 mins. After the reaction finished, the mixture was diluted with 100 ml water and pH was adjusted to neutral with concentrated hydrochloric acid, then stirred for 30 mins, large amount of yellow solid was precipitated, then filtering, the filter cake was washed with water twice and dried to give yellow solid of N-(3-chloro-4-fluorophenyl)-7-(3-morpholinopropoxy)-6-nitroquinazolin-4-amine (yield 90%).

Workup

  1. stirringthe mixture was stirred at room temperature for further 30 mins
  2. stirringstirred for 30 mins
  3. customlarge amount of yellow solid was precipitated
  4. filtrationfiltering
  5. washthe filter cake was washed with water twice
  6. customdried

Sources & evidence

ORD record
ord-bcba3220bfc145be89ee5b4da6d4edd3
Source dataset
uspto-grants-2016_06
Patent number
US09371292B2

Reaction notes

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