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1-Bromo-3-chloropropane → 2-[2-(3-chloro-4-fluorophenyl)-6-(3-chloropropoxy)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide

HRID 1157458
Notes
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Reaction equation

HRID 1157458 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:18]([CH2:19][C:20]([NH:22][CH:23]([CH3:25])[CH3:24])=[O:21])[C:17](=[O:26])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:27])[CH:15]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].Br[CH2:29][CH2:30][CH2:31][Cl:32].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:18]([CH2:19][C:20]([NH:22][CH:23]([CH3:24])[CH3:25])=[O:21])[C:17](=[O:26])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:27][CH2:29][CH2:30][CH2:31][Cl:32])[CH:15]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 595117832-[2-(3-chloro-4-fluorophenyl)-6-hydroxy-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide

Product 1

HCID 595117802-[2-(3-chloro-4-fluorophenyl)-6-(3-chloropropoxy)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamideYield 87.5%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A mixture of 2-[2-(3-chloro-4-fluorophenyl)-6-hydroxy-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (INTERMEDIATE IV.1) (373 mg, 0.96 mmol), 3-bromo-1-chloropropane (0.28 mL, 2.87 mmol) and K2CO3 (662 mg, 4.80 mmol) in acetonitrile (5 mL) was heated at reflux temperature for 24 h. The mixture was cooled to room temperature and then poured into ice water (40 mL). The resultant white solid was collected by filtration and washed with additional portions of cold water (3×20 mL) followed by washing with cold diethyl ether (3×10 mL) and cold hexane (2×10 mL) to remove residual 3-bromo-1-chloropropane. In this way 2-[2-(3-chloro-4-fluorophenyl)-6-(3-chloropropoxy)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (391 mg, 0.84 mmol, 87%) was obtained.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 24 h
  3. filtrationThe resultant white solid was collected by filtration
  4. washwashed with additional portions of cold water (3×20 mL)
  5. washby washing with cold diethyl ether (3×10 mL) and cold hexane (2×10 mL)
  6. customto remove residual 3-bromo-1-chloropropane

Sources & evidence

ORD record
ord-90d36b32533d4bf4a2cd51c32ccf3909
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07807686B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes