HCID 22732266, compound → HCID 136116301, compound

HRID 1357723Notes

Reaction equation

HRID 1357723 reaction equation
Cl.Cl.C([O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([NH:21][C:22]3[CH:27]=[C:26]([NH:28][C:29]([C:31]4[CH:36]=[CH:35][N:34]=[C:33]([N:37]5[CH2:42][CH2:41][O:40][CH2:39][CH2:38]5)[CH:32]=4)=[O:30])[CH:25]=[CH:24][C:23]=3[CH3:43])=[N:16][CH:17]=[N:18]2)=[CH:13][C:12]=1[O:44][CH3:45])C1C=CC=CC=1>FC(F)(F)C(O)=O>[OH:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([NH:21][C:22]3[CH:27]=[C:26]([NH:28][C:29]([C:31]4[CH:36]=[CH:35][N:34]=[C:33]([N:37]5[CH2:42][CH2:41][O:40][CH2:39][CH2:38]5)[CH:32]=4)=[O:30])[CH:25]=[CH:24][C:23]=3[CH3:43])=[N:16][CH:17]=[N:18]2)=[CH:13][C:12]=1[O:44][CH3:45]

Participants

3

Reactant 1

HCID 22732266HCID 22732266, compound

Product 1

HCID 136116301HCID 136116301, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 7-benzyloxy-6-methoxy-4-[2-methyl-5-(2-morpholinopyridine-4-carboxamido)anilino]quinazoline dihydrochloride (4.45 g) and trifluoroacetic acid (20 ml) was stirred and heated to reflux for 90 minutes. The mixture was cooled to ambient temperature and evaporated. A mixture of a dilute aqueous sodium bicarbonate solution and methylene chloride was added to the residue and the resultant mixture was stirred for 30 minutes at ambient temperature. The precipitated solid was collected, washed with water and dried under vacuum at 60° C. to give 7-hydroxy-6-methoxy-4-[2-methyl-5-(2-morpholinopyridine-4-carboxamido)anilino]quinazoline (3.67 g; NMR: 2.17 (s, 3H), 3.52 (t, 4H), 3.71 (t, 4H), 3.98 (s, 3H), 7.09 (d, 1H), 7.19 (s, 1H), 7.23 (s, 1H), 7.37 (d, 1H), 7.6 (d, 1H), 7.84 (s, 1H), 8.05 (s, 1H), 8.25 (d, 1H), 8.66 (s, 1H), 10.42 (s, 1H), 11.06 (s, 1H); m/s: M+H+ 487.

Workup

  1. temperatureheated
  2. temperatureto reflux for 90 minutes
  3. customevaporated
  4. additionA mixture of a dilute aqueous sodium bicarbonate solution and methylene chloride
  5. additionwas added to the residue
  6. stirringthe resultant mixture was stirred for 30 minutes at ambient temperature
  7. customThe precipitated solid was collected
  8. washwashed with water
  9. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-ec8fef20b0044be39f59587872480886
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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