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

HRID 2084018Notes

Reaction equation

HRID 2084018 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-c2e408f28bbf4a0886aea766c8e9aa89
Source dataset
uspto-grants-2004_04
Patent number
US06716847B2

Reaction notes

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