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Hydrochloric Acid → 4-(4-Chloro-2-fluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline hydrochloride

HRID 238102
Notes
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Reaction equation

HRID 238102 reaction equation
Cl.C(O)C.[Cl:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:19][CH:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]=[CH:8][N:7]=1.[Cl:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[C:30]([F:35])[CH:29]=1>C(O)(C)C.CCOCC>[ClH:5].[Cl:27][C:28]1[CH:34]=[CH:33][C:31]([NH:32][C:6]2[C:15]3[C:10](=[CH:11][C:12]([O:18][CH2:19][CH:20]4[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]4)=[C:13]([O:16][CH3:17])[CH:14]=3)[N:9]=[CH:8][N:7]=2)=[C:30]([F:35])[CH:29]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 938984-Chloro-2-fluoroanilineHCID 117822304-Chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline

Product 1

HCID 231333204-(4-Chloro-2-fluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline hydrochlorideYield 89.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

3.5M Hydrogen chloride in ethanol (75 μl, 0.26 mmol) was added to a suspension of 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (80 mg, 0.25 mmol), (prepared as described for the starting material in Example 2c), in isopropanol (3 ml), the mixture was heated to 50° C. and 4-chloro-2-fluoroaniline (44 mg, 0.3 mmol) was added. The mixture was heated at reflux for 30 minutes. After cooling, the mixture was diluted with ether (3 ml). The precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline hydrochloride (105 mg, 82%).

Workup

  1. custom(prepared
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 30 minutes
  4. temperatureAfter cooling
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-d370166b5619435f9afce9ad5251a956
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642608B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes