4-Chloro-6,7-dimethoxyquinazoline → HCID 22732275, compound

HRID 2084035Notes

Reaction equation

HRID 2084035 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:16][C:17]1[CH:18]=[C:19]([NH:23][C:24]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[CH:27]=2)=[O:25])[CH:20]=[CH:21][CH:22]=1>>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][N:3]=[C:2]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([N:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)[CH:27]=2)=[O:25])[CH:18]=1

Participants

3

Reactant 2

HCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 22238130N-(3-Aminophenyl)-2-(4-morpholinyl)-4-pyridinecarboxamide

Product 1

HCID 22732275HCID 22732275, compoundYield 33%

Procedure

Using an analogous procedure to that described in Example 26, 4-chloro-6,7-dimethoxyquinazoline was reacted with N-(3-aminophenyl)-2-morpholinopyridine-4-carboxamide. The material so obtained was purified by column chromatography eluting with 96:3:1 methylene chloride/methanol/saturated aqueous ammonium hydroxide. The material so obtained was triturated under methylene chloride to give the title compound in 33% yield; NMR: 3.51 (m, 4H), 3.71 (m, 4H), 3.93 (s, 3H), 3.96 (s, 3H), 7.11 (d, 1H), 7.18 (s, 1H), 7.24 (s, 1H), 7.35 (m, 1H), 7.44 (d, 1H), 7.57 (d, 1H), 7.86 (s, 1H), 8.23 (s, 1H), 8.29 (d, 1H), 8.46 (s, 1H), 9.49 (s, 1H), 10.34 (s, 1H); Mass: M+H+ 487.

Workup

  1. customThe material so obtained
  2. customwas purified by column chromatography
  3. washeluting with 96:3:1 methylene chloride/methanol/saturated aqueous ammonium hydroxide
  4. customThe material so obtained
  5. customwas triturated under methylene chloride

Sources & evidence

ORD record
ord-f875100b90cb4fd2989522344a79be3d
Source dataset
uspto-grants-2004_04
Patent number
US06716847B2

Reaction notes

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