Isopropylamine → HCID 54258746, compound

HRID 1791824Notes

Reaction equation

HRID 1791824 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1OC[C@H]1CO1)[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.C(N)(C)C>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=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

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 53955805HCID 53955805, compound

Product 1

HCID 54258746HCID 54258746, compoundYield 120.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of (2R)-6-methoxy-4-(2-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (250 mg, 0.66 mmol), (prepared as described for the starting material in Example 269), and isopropylamine (1.5 ml) in THF (10 ml) was stirred at 75° C. for 18 hours under an atmosphere of nitrogen and then allowed to cool to ambient temperature. The mixture was filtered and the filtrate evaporated in vacuo. The residue was purified by silica gel chromatography using gradient elution with dichloromethane/methanolic ammonia (7M) (100/0 to 90/10) to give (2R)-7-(2-hydroxy-3-isopropylamino)propoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (243 mg, 84%).

Workup

  1. custom(prepared
  2. temperatureto cool to ambient temperature
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washelution with dichloromethane/methanolic ammonia (7M) (100/0 to 90/10)

Sources & evidence

ORD record
ord-e77f24628f9d42b98aee2741e0f2b855
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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