Ammonia → 6-Hydroxy-7-methoxy-4-[2-methyl-5-(2-morpholinopyridine-4-carboxamido)anilino]quinazoline

HRID 1357709Notes

Reaction equation

HRID 1357709 reaction equation
Cl.Cl.C([O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[N:13]=[CH:12][N:11]=[C:10]2[NH:19][C:20]1[CH:25]=[C:24]([NH:26][C:27]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH:30]=2)=[O:28])[CH:23]=[CH:22][C:21]=1[CH3:41])(=O)C.N>>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[N:13]=[CH:12][N:11]=[C:10]2[NH:19][C:20]1[CH:25]=[C:24]([NH:26][C:27]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([N:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)[CH:30]=2)=[O:28])[CH:23]=[CH:22][C:21]=1[CH3:41]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 227322476-Acetoxy-7-methoxy-4-[2-methyl-5-(2-morpholinopyridine-4-carboxamido)anilino]quinazoline Dihydrochloride

Product 1

HCID 227322826-Hydroxy-7-methoxy-4-[2-methyl-5-(2-morpholinopyridine-4-carboxamido)anilino]quinazolineYield 78.3%

Conditions

Temperature
50 °C

Procedure

A mixture of 6-acetoxy-7-methoxy-4-[2-methyl-5-(2-morpholinopyridine-4-carboxamido)anilino]quinazoline dihydrochloride (150 mg) and methanolic ammonia (2 ml) was stirred and heated to 50° C. for 48 hours. The mixture was allowed to cool to ambient temperature and the resultant solid was isolated and washed with diethyl ether (10 ml). There was thus obtained the title compound (95 mg, 78%); NMR: 2.12 (s, 3H), 3.51 (m, 4H), 3.7 (m, 4H), 3.97 (s, 3H), 7.09 (m, 1H), 7.12 (s, 1H), 7.23 (m, 2H), 7.57 (m, 1H), 7.69 (s, 1H), 7.72 (m, 1H), 8.23 (s, 1H), 8.26 (m, 1H), 9.17 (s, 1H), 10.28 (s, 1H); m/s: M+H+ 487.

Workup

  1. temperatureto cool to ambient temperature
  2. customthe resultant solid was isolated
  3. washwashed with diethyl ether (10 ml)

Sources & evidence

ORD record
ord-7e38d72e8806455d94028615b6ec25b5
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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