1-(2-Methoxyethyl)piperazine → methyl 4-methyl-3-[6-(4-(2-methoxyethyl)piperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoate

HRID 641956Notes

Reaction equation

HRID 641956 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.Br[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[CH:17][N:16]([C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][C:31]=1[CH3:32])[C:25]([O:27][CH3:28])=[O:26])[C:15]2=[O:33]>>[CH3:32][C:31]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[N:16]1[C:15](=[O:33])[C:14]2[C:19](=[CH:20][CH:21]=[C:12]([N:8]3[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH2:6][CH2:7]3)[CH:13]=2)[N:18]=[CH:17]1

Participants

3

Reactant 2

HCID 27346381-(2-Methoxyethyl)piperazineHCID 66919066Methyl 3-(6-bromo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate

Product 1

HCID 68603298methyl 4-methyl-3-[6-(4-(2-methoxyethyl)piperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoate

Procedure

Using an analogous procedure to that described paragraph (B) in the portion of Example 1 which is concerned with the preparation of starting material N-(2-methoxyethyl)piperazine was reacted with methyl 3-(6-bromo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate to give methyl 4-methyl-3-[6-(4-(2-methoxyethyl)piperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoate; NMR Spectrum: (DMSOd6) 2.18 (s, 3H), 2.55 (t, 2H), 2.60 (m, 4H), 3.25 (s, 3H), 3.27 (m, 4H), 3.50 (t, 2H), 3.88 (s, 3H), 7.47 (s, 1H), 7.62 (m, 3H), 7.97 (s, 1H), 8.01 (m, 1H), 8.09 (s, 1H); Mass Spectrum: M+H+ 437.

Sources & evidence

ORD record
ord-f3c1c2ea3b384ef79b9d99f30745581e
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

Loading…