2-Methyl-1-(propan-2-yl)piperazine → 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-[(3-methylpiperazin-1-yl)methyl]-3,4-dihydroquinazolin-2(1H)-one

HRID 394102Notes

Reaction equation

HRID 394102 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([CH:18]=O)[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:28])[N:13]2[C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:27].C([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH:33]1[CH3:38])(C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([CH2:18][N:35]2[CH2:36][CH2:37][NH:32][CH:33]([CH3:38])[CH2:34]2)[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:28])[N:13]2[C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:27]

Participants

3

Reactant 2

HCID 177503702-Methyl-1-(propan-2-yl)piperazineHCID 226481625-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carbaldehyde

Product 1

HCID 101861125-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-[(3-methylpiperazin-1-yl)methyl]-3,4-dihydroquinazolin-2(1H)-one

Procedure

The title compound was prepared from 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carbaldehyde (INTERMEDIATE AAA 1) and 1-isopropyl-2-methylpiperazine as described in EXAMPLE AAA1, STEP A. 1H NMR (CDCl3, 500 MHz): δ 0.90 (brs, 3H), 0.93 (brs, 3H), 0.98 (brs, 3H), 1.92 (brs, 1H), 2.16 (brs, 1H), 2.31 (brs, 1H), 2.57 (m, 2H), 2.67 (brs, 1H), 3.21 (brs, 1H), 3.40 (s, 2H), 4.22-4.485 (m, 2H), 5.05 (s, 1H), 6.17 (s, 1H), 6.85 (d, 1H, J=3.7 Hz), 7.30-7.60 (m, 7H). MS (API-ES+): 559 (M+H).

Sources & evidence

ORD record
ord-26bdeec6f850484fb52855afbd73fa41
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

Loading…