Potassium Carbonate → HCID 69089727, compound

HRID 1791679Notes

Reaction equation

HRID 1791679 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](OC)[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:24](=O)([O-])[O-:25].[K+].[K+].ClC1C=C(O)C=C2C=1NC(C(OCC)=O)=C2>CC(N(C)C)=O>[NH3:3].[CH3:24][O:25][C:4]1[N:3]=[CH:2][C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)=[CH:9][CH:10]=2)[N:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 110021914-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazolineHCID 22030936Ethyl 7-chloro-5-hydroxyindole-2-carboxylate

Product 2

HCID 222AmmoniaYield 2%HCID 69089727HCID 69089727, compoundYield 215.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

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

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

Sources & evidence

ORD record
ord-5420ffa646cf4180bb04913a9b4e2ddb
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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