Thionyl Chloride → 4-Chloro-6-methoxy-7-(2-(imidazol-1-yl)ethoxy)quinazoline

HRID 1597258Notes

Reaction equation

HRID 1597258 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13](=O)[NH:14][CH:15]=[N:16]3)=[CH:11][C:10]=2[O:20][CH3:21])[CH:5]=[CH:4][N:3]=[CH:2]1.S(Cl)([Cl:24])=O>>[Cl:24][C:13]1[C:12]2[C:17](=[CH:18][C:9]([O:8][CH2:7][CH2:6][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[C:10]([O:20][CH3:21])[CH:11]=2)[N:16]=[CH:15][N:14]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 1354908447-(2-(Imidazol-1-yl)ethoxy)-6-methoxy-3,4-dihydroquinazolin-4-one

Product 1

HCID 111412614-Chloro-6-methoxy-7-(2-(imidazol-1-yl)ethoxy)quinazoline

Procedure

Using a procedure analogous to the one described for the synthesis of Example 23, 7-(2-(imidazol-1-yl)ethoxy)-6-methoxy-3,4-dihydroquinazoline-4-one (286 mg, 1 mmol) was reacted with thionyl chloride (50 ml) to give 4-chloro-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline which was then reacted with 5,7-diaza-6-methyloxindole (440 mg, 3 mmol) and sodium hydride (120 mg, 3 mmol) to give 4-(5,7-diaza-6-methyloxindol-3-yl)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline hydrochloride (80 mg, 15%).

Sources & evidence

ORD record
ord-a29eb36de6b64a1097f291050aa8e2d3
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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