Isopropylamine → HCID 22030536, compound

HRID 1791670Notes

Reaction equation

HRID 1791670 reaction equation
[O:1]1[CH2:28][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][C:20]([CH3:25])=[CH:19]4)=[N:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:26][CH3:27].[CH:29]([NH2:32])([CH3:31])[CH3:30]>CN(C=O)C>[OH:1][CH:2]([CH2:28][NH:32][CH:29]([CH3:31])[CH3:30])[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][C:20]([CH3:25])=[CH:19]4)=[N:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:26][CH3:27]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 22030772HCID 22030772, compound

Product 1

HCID 22030536HCID 22030536, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 7-(2,3-epoxypropoxy)-6-methoxy-4-(2-methylindol-5-yloxy) quinazoline (100 mg, 0.27 mmol), (prepared as described for the starting material in Example 162), and isopropylamine (100 ul, 0.8 mmol) in DMF (4 ml) was heated at 70° C. for 24 hours. The solvent was removed by evaporation and the residue was purified by silica column chromatography eluting with dichloromethane/methanol/0.880 aqueous ammonia (100/8/1) to give 7-(2-hydroxy-3-(isopropylamino)propoxy)-6-methoxy-4(2-methylindol-5-yloxy)quinazoline (18 mg, 16%).

Workup

  1. custom(prepared
  2. customThe solvent was removed by evaporation
  3. customthe residue was purified by silica column chromatography
  4. washeluting with dichloromethane/methanol/0.880 aqueous ammonia (100/8/1)

Sources & evidence

ORD record
ord-7c1252df20534aecbea6a4ad46e7aa95
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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