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3-Morpholino-1-propanol → 4-[(3-Bromophenyl)amino]7-[(3-morpholino)propyloxy]-6-nitroquinazoline

HRID 1698949
Notes
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Reaction equation

HRID 1698949 reaction equation
[Na].[O:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][OH:11])[CH2:4][CH2:3]1.[Br:12][C:13]1[CH:14]=[C:15]([NH:19][C:20]2[C:29]3[C:24](=[CH:25][C:26](F)=[C:27]([N+:30]([O-:32])=[O:31])[CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH:16]=[CH:17][CH:18]=1>C1COCC1.O>[Br:12][C:13]1[CH:14]=[C:15]([NH:19][C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:11][CH2:10][CH2:9][CH2:8][N:5]4[CH2:6][CH2:7][O:2][CH2:3][CH2:4]4)=[C:27]([N+:30]([O-:32])=[O:31])[CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH:16]=[CH:17][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1995763-Morpholino-1-propanolHCID 5360545SodiumHCID 10761182N-(3-Bromophenyl)-7-fluoro-6-nitroquinazolin-4-amine

Product 1

HCID 106726284-[(3-Bromophenyl)amino]7-[(3-morpholino)propyloxy]-6-nitroquinazolineYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
20 °C

Procedure

Sodium metal (27.6 mmol, 0.63 g) was added to a solution of 3-morpholinopropan-1-ol (22.0 mmol, 3.20 g) in THF (60 mL) under N2. The resulting suspension was stirred at 20° C. for 2 hours and then cannulated into a solution of 4-[(3-bromophenyl)amino]-7-fluoro-6-nitroquinazoline, J Med Chem, 1996(39):918) (2.0 g, 5.51 mmol) in THF (50 mL) under N2. The solution was then heated at reflux for 24 hours before being diluted with water and extracted with EtOAc. The combined organic extracts were dried over anhydrous Na2SO4, concentrated under reduced pressure and chromatographed on alumina eluting with EtOAc/hexane (1:1) to MeOH/CH2Cl2/EtOAc (2:3:5) to give 4-[(3-bromophenyl)amino]7-[(3-morpholino)propyloxy]-6-nitroquinazoline (1.75 g, 65%) as a yellow powder, mp (MeOH) 216-220° C.

Workup

  1. temperatureThe solution was then heated
  2. temperatureat reflux for 24 hours
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on alumina eluting with EtOAc/hexane (1:1) to MeOH/CH2Cl2/EtOAc (2:3:5)

Sources & evidence

ORD record
ord-49c53e1df1d04b21b0eb00386e940407
Source dataset
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06344459B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes