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Hydrochloric Acid → 4-(4-Chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(2-(4-methylpiperazin-1-yl)ethoxy)quinazoline

HRID 634705
Notes
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Reaction equation

HRID 634705 reaction equation
[ClH:1].Cl[C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1.Br[C:26]1[C:32]([OH:33])=[CH:31][C:29]([NH2:30])=[C:28]([F:34])[CH:27]=1>C(O)(C)C.CC(C)=O>[Cl:1][C:26]1[C:32]([OH:33])=[CH:31][C:29]([NH:30][C:3]2[C:12]3[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=[CH:5][N:4]=2)=[C:28]([F:34])[CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 109656515-Amino-2-bromo-4-fluorophenolHCID 117594994-Chloro-6-methoxy-7-(2-(4-methylpiperazin-1-yl)ethoxy)quinazoline

Product 1

HCID 212603034-(4-Chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(2-(4-methylpiperazin-1-yl)ethoxy)quinazolineYield 32%

Reagents, catalysts & solvents 2

HCID 180
Acetone
Solvent
HCID 3776IsopropanolSolvent

Procedure

1M Ethereal hydrogen chloride (0.34 ml, 0.34 mmol) was added to 4-chloro-6-methoxy-7-(2-(4-methylpiperazin-1-yl)ethoxy)quinazoline (115 mg, 0.34 mmol) and 4-chloro-2-fluoro-5-hydroxyaniline (61 mg, 0.38 mmol), (as described in EP 61741 A2), in isopropanol (5 ml) and the mixture was heated at reflux for 90 minutes and then allowed to cool. The mixture was diluted with acetone, and the solid product collected by filtration. The impure solid was treated with methylene chloride/methanol/ammonia (100/8/1) (5 ml), and water was added. The reprecipitated product was collected by filtration and dried to give 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(2-(4-methylpiperazin-1-yl)ethoxy)quinazoline (32%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 90 minutes
  3. temperatureto cool
  4. filtrationthe solid product collected by filtration
  5. additionThe impure solid was treated with methylene chloride/methanol/ammonia (100/8/1) (5 ml), and water
  6. additionwas added
  7. filtrationThe reprecipitated product was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-0fcdfa069c1845a0a3c4370f16bc440a
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06184225B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes