Potassium Carbonate → 4-(7-Azaindol-5-yloxy)-7-{3-[4-(tert-butoxycarbonyl)piperazin-1-yl]propoxy}-6-methoxyquinazoline

HRID 916462Notes

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][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:31][C:32]1[CH:33]=[C:34]2[C:38](=[N:39][CH:40]=1)[NH:37][CH:36]=[CH:35]2.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[NH:37]1[C:38]2[C:34](=[CH:33][C:32]([O:31][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]5[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]5)=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)=[CH:40][N:39]=2)[CH:35]=[CH:36]1

Participants

Conditions

Temperature: 85 °C

Procedure

tert-Butyl 4-{3-[(4-chloro-6-methoxyquinazolin-7-yl)oxy]propyl}piperazine-1-carboxylate (2.0 g, 4.42 mmol) was dissolved in N,N-dimethylacetamide (60 ml) and 5-hydroxy-7-azaindole (651 mg, 4.86 mmol), (prepared as described for the starting material in Example 2), and potassium carbonate (671 mg, 4.86 mmol) added. The reaction mixture was heated at 85° C. for 3 hours. The mixture was cooled, filtered and concentrated under reduced pressure. Column chromatography of the residue (8-10% methanol/dichloromethane) gave 4-(7-azaindol-5-yloxy)-7-{3-[4-(tert-butoxycarbonyl)piperazin-1-yl]propoxy}-6-methoxyquinazoline (2.0 g, 85%) as a white solid.

Workup

additionadded
temperatureThe mixture was cooled
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-4971a3c2c94c44d4af9226265346b9e3
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268230B2

Reaction notes

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