5-Amino-4-fluoro-2-methylphenol → ZM 323881 hydrochloride

HRID 279632Notes

Reaction equation

HRID 279632 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:6]([OH:10])=[CH:5][C:3]=1[NH2:4].Cl.[CH2:12]([O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24]([Cl:30])=[N:25][CH:26]=[N:27]2)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(O)CCC>[ClH:30].[CH2:12]([O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24]([NH:4][C:3]3[CH:5]=[C:6]([OH:10])[C:7]([CH3:9])=[CH:8][C:2]=3[F:1])=[N:25][CH:26]=[N:27]2)=[CH:22][CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 101540985-Amino-4-fluoro-2-methylphenolHCID 226250837-Benzyloxy4-chloroquinazoline hydrochloride

Product 1

HCID 22624897ZM 323881 hydrochlorideYield 80.4%

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Conditions

Temperature
120 °C

Procedure

2-Fluoro-5-hydroxy-4-methylaniline (170 mg, 1.2 mmol), (prepared as described for the starting material in Example 13), was added to a solution of 7-benzyloxy-4-chloroquinazoline hydrochloride (307 mg, 1mmol) in 2-pentanol (5 ml) and the mixture stirred at 120° C. for 2 hours. The mixture was allowed to cool and the resulting precipitate was collected by filtration, washed with isopropanol and then ether and dried under vacuum at 70° C. to give 7-benzyloxy-4-(2-fluoro-5-hydroxy-4-methylanilino)quinazoline hydrochloride (331 mg, 80%).

Workup

  1. temperatureto cool
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with isopropanol
  4. dry with materialether and dried under vacuum at 70° C.

Sources & evidence

ORD record
ord-33d2f28668ee4906abb57def8b87e20b
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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