1-Ethylpiperazine → methyl 4-methyl-3-[6-(4-ethylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoate

HRID 641953Notes

Reaction equation

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

Participants

Reactant 2

HCID 791961-Ethylpiperazine

HCID 66919066Methyl 3-(6-bromo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate

Product 1

HCID 68604407methyl 4-methyl-3-[6-(4-ethylpiperazin-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-ethylpiperazine was reacted with methyl 3-(6-bromo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate to give methyl 4-methyl-3-[6-(4-ethylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoate; NMR Spectrum: (DMSOd6) 1.05 (t, 3H), 2.17 (s, 3H), 2.40 (m, 2H), 2.53 (m, 4H), 3.29 (m, 4H), 3.87 (s, 3H), 7.48 (s, 1H), 7.63 (m, 3H), 7.97 (s, 1H), 8.02 (d, 1H), 8.10 (d, 1H); Mass Spectrum: M+H+ 407.

Sources & evidence

ORD record: ord-570ef45c00b44a199ba6cd4a0347621a
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696215B2

Reaction notes

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