Potassium Carbonate → 6-Methoxy-4-(3-methylindol-5-yloxy)-7-(3-piperidinopropoxy)quinazoline

HRID 454172Notes

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][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[C:37]([OH:40])[CH:38]=2)[NH:33][CH:32]=1>CC(N(C)C)=O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[N:5]=[CH:4][N:3]=[C:2]2[O:40][C:37]1[CH:38]=[C:39]2[C:34](=[CH:35][CH:36]=1)[NH:33][CH:32]=[C:31]2[CH3:30]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (168 mg, 0.5 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (207 mg, 1.5 mmol), 3-methyl-5-hydroxyindole (88 mg, 0.6 mmol), (Can. J. Chem. 1964, 42, 514), and DMA (2.0 ml) was purged with nitrogen for 5 minutes at 25° C. This mixture was then stirred at 100° C. for 3 hours then allowed to cool to ambient temperature, was filtered and the filtrate evaporated under vacuum. The residue was purified by silica column chromatography eluting with dichloromethane/methanolic ammonia (7M) (90/10) to give 6-methoxy-4-(3-methylindol-5-yloxy)-7-(3-piperidinopropoxy)quinazoline (155 mg, 69%).

Workup

custom(prepared
customwas purged with nitrogen for 5 minutes at 25° C
temperatureto cool to ambient temperature
filtrationwas filtered
customthe filtrate evaporated under vacuum
customThe residue was purified by silica column chromatography
washeluting with dichloromethane/methanolic ammonia (7M) (90/10)

Sources & evidence

ORD record: ord-e46e77ec694543c79f851034faddb33e
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492560B2

Reaction notes

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