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

HRID 1791638Notes

Reaction equation

HRID 1791638 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([O:11]C1C3C(=CC(OCC4CCNCC4)=CC=3)N=CN=1)=[CH:6][CH:5]=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](OC4C=C5C(=CC=4)NC(C)=C5)=[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[CH2:39][CH2:38][NH:37][CH2:42][CH2:41]1)[N:53]=[C:52]([O:11][C:7]1[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=1)[NH:3][C:2]([CH3:1])=[CH:10]3)[N:51]=[CH:50]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 867601626-Methoxy (2-methylindol-5yloxy)-7-(2-(piperidin-4-yl)ethoxy)quinazolineYield 87%

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 (2-methylindol-5yloxy)-7-(2-(piperidin-4-yl)ethoxy)quinazoline (284 mg, 87%).

Sources & evidence

ORD record
ord-6921e7f806d94a5999c24a7292ff9bf9
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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