4-Chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline → 4-(2,3-Dimethylindol-5-yloxy)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline

HRID 1791574Notes

Reaction equation

HRID 1791574 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.[CH3:23][C:24]1[NH:25][C:26]2[C:31]([C:32]=1[CH3:33])=[CH:30][C:29]([OH:34])=[CH:28][CH:27]=2>>[CH3:23][C:24]1[NH:25][C:26]2[C:31]([C:32]=1[CH3:33])=[CH:30][C:29]([O:34][C:2]1[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]4[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][N:3]=1)=[CH:28][CH:27]=2

Participants

3

Reactant 2

HCID 117822304-Chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolineHCID 220307882,3-Dimethyl-1H-indol-5-ol

Product 1

HCID 220306684-(2,3-Dimethylindol-5-yloxy)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazolineYield 40%

Procedure

Using an analogous procedure to that described in Example 34, 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (110 mg, 0.34 mmol), (prepared as described for the starting material in Example 10), was reacted with 2,3-dimethyl-5-hydroxyindole (66 mg, 0.41 mmol), (Arch. Pharm. 1972, 305, 159). The crude product was purified by column chromatography eluting with methanol/methylene chloride (1/9) followed by 3M ammonia in methanol/methanol/methylene chloride (5/15/80) to give 4-(2,3-dimethylindol-5-yloxy)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (60 mg, 40%).

Workup

  1. custom(prepared
  2. customThe crude product was purified by column chromatography
  3. washeluting with methanol/methylene chloride (1/9)

Sources & evidence

ORD record
ord-c7c6aa780474464098c7bfbbaec7ba8d
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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