4-Chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline → HCID 22030895, compound

HRID 1791708Notes

Reaction equation

HRID 1791708 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:23][C:24]1[CH:33]=[CH:32][C:27]2[N:28]=[C:29]([CH3:31])[NH:30][C:26]=2[CH:25]=1>>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)[N:5]=[CH:4][N:3]=[C:2]2[O:23][C:24]1[CH:33]=[CH:32][C:27]2[N:28]=[C:29]([CH3:31])[NH:30][C:26]=2[CH:25]=1

Participants

3

Reactant 2

HCID 117822304-Chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolineHCID 133725342-Methyl-1H-benzimidazol-6-ol

Product 1

HCID 22030895HCID 22030895, compoundYield 25%

Procedure

Using an analogous procedure to that described in Example 189, 4-chloro-6-methoxy-7-(1-methylpiperidin-4-yl)methoxyquinazoline, (prepared as described for the starting material in Example 10); was reacted with 5-hydroxy-2-methylbenzimidazole (200 mg, 0.62 mmol) and after work-up and purification on a 10 g silica ISOLUTE column using successively dichloromethane, dichloromethane/methanol (95/5) and dichloromethane/methanol saturated with ammonia (95/5), gave 6-methoxy-4-(2-methyl-1H-benzimidazol-6-yloxy)-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (68 mg, 25%).

Workup

  1. custom(prepared
  2. customafter work-up and purification on a 10 g silica ISOLUTE column

Sources & evidence

ORD record
ord-bc76adc5b0bd4925b3e61eaf2710b807
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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