4-Bromo-2-fluoroaniline → 7-Benzyloxy4-(4-bromo-2-fluoroanilino)-6-methoxyquinazoline hydrochloride

HRID 577356Notes

Reaction equation

HRID 577356 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:20])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[C:26]([F:31])[CH:25]=1>CC(O)C>[ClH:20].[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:28][C:27]3[CH:29]=[CH:30][C:24]([Br:23])=[CH:25][C:26]=3[F:31])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 1230504-Bromo-2-fluoroanilineHCID 220308367-(Benzyloxy)-4-chloro-6-methoxyquinazoline hydrochloride

Product 1

HCID 187534737-Benzyloxy4-(4-bromo-2-fluoroanilino)-6-methoxyquinazoline hydrochlorideYield 78%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 7-benzyloxy-4-chloro-6-methoxyquinazoline hydrochloride (8.35 g, 27.8 mmol), (prepared, for example, as described in WO 97/22596, Example 1), and 4-bromo-2-fluoroaniline (5.65 g, 29.7 mmol) in 2-propanol (200 ml) was heated at reflux for 4 hours. The resulting precipitate was collected by filtration, washed with 2-propanol and then ether and dried under vacuum to give 7-benzyloxy-4-(4-bromo-2-fluoroanilino)-6-methoxyquinazoline hydrochloride (9.46 g, 78%).

Workup

  1. temperatureat reflux for 4 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with 2-propanol
  4. dry with materialether and dried under vacuum

Sources & evidence

ORD record
ord-30da32675c744749983f8ddd71b01261
Source dataset
uspto-grants-2015_05
Patent number
US09040548B2

Reaction notes

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