7-(2-(1-Tert-butoxycarbonylpiperidin-4-yl)ethoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline → 6-Methoxy-4-(2-methylindol-5-yloxy)-7-(2-(piperidin-4-yl)ethoxy)quinazoline

HRID 454105Notes

Reaction equation

HRID 454105 reaction equation
CC1NC2C(C=1)=CC(OC1C3C(=CC(OCC4CCNCC4)=CC=3)N=CN=1)=CC=2.C(OC([N:37]1[CH2:42][CH2:41][CH:40]([CH2:43][CH2:44][O:45][C:46]2[CH:55]=[C:54]3[C:49]([C:50]([O:56][C:57]4[CH:58]=[C:59]5[C:63](=[CH:64][CH:65]=4)[NH:62][C:61]([CH3:66])=[CH:60]5)=[N:51][CH:52]=[N:53]3)=[CH:48][C:47]=2[O:67][CH3:68])[CH2:39][CH2:38]1)=O)(C)(C)C>>[CH3:68][O:67][C:47]1[CH:48]=[C:49]2[C:54](=[CH:55][C:46]=1[O:45][CH2:44][CH2:43][CH:40]1[CH2:41][CH2:42][NH:37][CH2:38][CH2:39]1)[N:53]=[CH:52][N:51]=[C:50]2[O:56][C:57]1[CH:58]=[C:59]2[C:63](=[CH:64][CH:65]=1)[NH:62][C:61]([CH3:66])=[CH:60]2

Participants

3

Reactant 2

HCID 220306867-(2-(1-Tert-butoxycarbonylpiperidin-4-yl)ethoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazolineHCID 220308754-(2-Methylindol-5-yloxy)-7-(piperidin-4-ylmethoxy)quinazoline

Product 1

HCID 220307796-Methoxy-4-(2-methylindol-5-yloxy)-7-(2-(piperidin-4-yl)ethoxy)quinazolineYield 87.5%

Procedure

Using an analogous procedure to that described for the synthesis of 4-(2-methylindol-5-yloxy)-7-(piperidin-4-ylmethoxy)quinazoline, (prepared as described in Example 122), 7-(2-(1-tert-butoxycarbonylpiperidin-4-yl)ethoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (400 mg, 0.75 mmol), (prepared as described in Example 126), was used to give 6-methoxy-4-(2-methylindol-5-yloxy)-7-(2-(piperidin-4-yl)ethoxy)quinazoline (284 mg, 87%).

Sources & evidence

ORD record
ord-06652084f90a4b649526b9f2939f1ce9
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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