Tetrahydrofuran → HCID 69664036, compound

HRID 1791821Notes

Reaction equation

HRID 1791821 reaction equation
CO[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.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.C1C[O:37][CH2:36]C1>>[OH:16][C@@H:15]([CH2:17][N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)[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][C:8]([O:37][CH3:36])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 31268PyrrolidineHCID 23537223HCID 23537223, compound

Product 1

HCID 69664036HCID 69664036, compoundYield 36%

Conditions

Temperature
75 °C

Procedure

A mixture of (2S)-6-methoxy-4-(2-methylindol-5-yloxy)-7-(oxiran-2ylmethoxy)quinazoline (250 mg, 0.66 mmol), and pyrrolidine (1.5 ml) in THF (10 ml) was stirred at 75° C. for 3 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 (2S)-7-(2-hydroxy-3-(pyrrolidin-1-yl)propoxy)-methoxy-4-(2-methylindol-5-yloxy)quinazoline (106 mg, 36%).

Workup

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

Sources & evidence

ORD record
ord-6b9629aaad264eb587e7df0db68d2700
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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