Diethylamine → HCID 57200809, compound

HRID 1791783Notes

Reaction equation

HRID 1791783 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][C@H:15]1[CH2:17][O:16]1)[N:9]=[CH:8][N:7]=[C:6]2[O:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([CH3:28])=[CH:22]2.[CH2:29]([NH:31][CH2:32][CH3:33])[CH3:30]>CN(C=O)C>[CH2:29]([N:31]([CH2:17][C@@H:15]([OH:16])[CH2:14][O:13][C:12]1[CH:11]=[C:10]2[C:5]([C:6]([O:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23]([CH3:28])=[CH:22]4)=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:2][CH3:1])[CH2:32][CH3:33])[CH3:30]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 53955805HCID 53955805, compound

Product 1

HCID 57200809HCID 57200809, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (2R)-6-methoxy-4-(2-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (300 mg, 0.79 mmol), (prepared as described for the starting material in Example 269), and diethylamine (0.25 ml, 2.38 mmol) in DMF (10 ml) was stirred at 70° C. for 24 hours and allowed to cool to ambient temperature. The solvents were removed in vacuo and the residue purified by silica column chromatography, gradient elution (dichloromethane, 5% methanol/95% dichloromethane, dichloromethane/methanol/0.88 ammonia (100/8/1)) to give (2R)-7-(3-(N,N-diethylamino)-2-hydroxypropoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (288 mg, 81%).

Workup

  1. custom(prepared
  2. temperatureto cool to ambient temperature
  3. customThe solvents were removed in vacuo
  4. customthe residue purified by silica column chromatography, gradient elution (dichloromethane, 5% methanol/95% dichloromethane, dichloromethane/methanol/0.88 ammonia (100/8/1))

Sources & evidence

ORD record
ord-ecdf3e68612844bfb6627c1e01714b97
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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