HCID 22030610, compound → HCID 135763121, compound

HRID 454194Notes

Reaction equation

HRID 454194 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:29]=[C:28]4[C:23]([CH:24]=[CH:25][CH:26]=[N:27]4)=[CH:22][CH:21]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31])C1C=CC=CC=1>FC(F)(F)C(O)=O>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:29]=[C:28]4[C:23]([CH:24]=[CH:25][CH:26]=[N:27]4)=[CH:22][CH:21]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31]

Participants

3

Reactant 1

HCID 22030610HCID 22030610, compound

Product 1

HCID 135763121HCID 135763121, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-benzyloxy-6-methoxy-4-(quinolin-7-yloxy)quinazoline (1.50 g, 3.70 mmol), (prepared as described in Example 196), in trifluoroacetic acid (50 ml) was heated at reflux for 150 minutes. The reaction was concentrated in vacuo and the reaction neutralised with saturated aqueous ammonium hydroxide. The resulting precipitate was filtered, washed with acetone and dried under suction to give 7-hydroxy-6-methoxy-4-(quinolin-7-yloxy)quinazoline (0.90 g, 2.82 mmol, 76%) as a white solid.

Workup

  1. temperatureat reflux for 150 minutes
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe reaction neutralised with saturated aqueous ammonium hydroxide
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with acetone
  6. customdried under suction

Sources & evidence

ORD record
ord-e5804af195634958a281f83bd0c94636
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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