4-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline → HCID 22732287, compound

HRID 1357725Notes

Reaction equation

HRID 1357725 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:24][C:25]1[CH:26]=[C:27]([NH:31][C:32](=[O:41])[C:33]2[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=2)[CH:28]=[CH:29][CH:30]=1>>[C:39]([C:36]1[CH:35]=[CH:34][C:33]([C:32]([NH:31][C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([CH:26]=2)[NH:24][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)=[O:41])=[CH:38][CH:37]=1)#[N:40]

Participants

3

Reactant 2

HCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolineHCID 16785182HCID 16785182, compound

Product 1

HCID 22732287HCID 22732287, compoundYield 48%

Procedure

Using an analogous procedure to that described in Example 26, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline was reacted with N-(3-aminophenyl)-4-cyanobenzamide. The material so obtained was purified by column chromatography eluting with 85:10:5 methylene chloride/methanol/isopropylamine. The material so obtained was triturated under diethyl ether to give the title compound in 48% yield; NMR: 2.1 (m, 2H), 3.35-3.45 (m, 4H), 3.7-3.8 (m, 8H), 3.98 (s, 3H), 4.22 (m, 2H), 7.2 (s, 1H), 7.38 (m, 1H), 7.51 (m, 1H), 7.58 (m, 1H), 7.93 (s, 1H), 8.04 (d, 2H), 8.13 (d, 2H), 8.31 (s, 1H), 8.46 (s, 1H), 9.59 (s, 1H); Mass: M+H+ 539.

Workup

  1. customThe material so obtained
  2. customwas purified by column chromatography
  3. washeluting with 85:10:5 methylene chloride/methanol/isopropylamine
  4. customThe material so obtained
  5. customwas triturated under diethyl ether

Sources & evidence

ORD record
ord-79d50be782174d47b5d020bea69f12d5
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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