Potassium Carbonate → HCID 22030822, compound

HRID 454154Notes

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+].[Cl:30][C:31]1[CH:32]=[C:33]([OH:45])[CH:34]=[C:35]2[C:39]=1[NH:38][C:37]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:36]2>CC(N(C)C)=O>[NH3:3].[Cl:30][C:31]1[CH:32]=[C:33]([O:45][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH:34]=[C:35]2[C:39]=1[NH:38][C:37]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:36]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (84 mg, 0.24 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (162 mg, 1.18 mmol) and ethyl 7-chloro-5-hydroxyindole-2-carboxylate (62 mg, 0.26 mmol) in DMA (2.0 ml) was stirred at 100° C. for 2 hours and allowed to cool to ambient temperature. The reaction mixture was filtered and the filtrate evaporated. The residue was purified by silica column chromatography using gradient elution dichloromethane with 2.5%, 5%, 10% methanol, then dichloromethane with 2% ammonia) to give 4-(7-chloro-2-(ethoxycarbonyl)indol-5-yloxy)-6-methoxy-7-(3-piperidinopropoxy)quinazoline (78 mg, 63%).

Workup

custom(prepared
temperatureto cool to ambient temperature
filtrationThe reaction mixture was filtered
customthe filtrate evaporated
customThe residue was purified by silica column chromatography
washelution dichloromethane with 2.5%, 5%, 10% methanol

Sources & evidence

ORD record: ord-3b34273d540241438c8cf38e945717d6
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492560B2

Reaction notes

Loading…