5-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carbaldehyde → 1-Allyl 2-tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}piperazine-1,2-dicarboxylate

HRID 394103Notes

Reaction equation

HRID 394103 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].[CH2:29]([O:32][C:33]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH:36]1[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[O:34])[CH:30]=[CH2:31]>>[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:38]2[CH2:39][CH2:40][N:35]([C:33]([O:32][CH2:29][CH:30]=[CH2:31])=[O:34])[CH:36]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37]2)[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:28])[N:13]2[C:20]1[C:21]([Cl:27])=[CH:22][CH:23]=[CH:24][C:25]=1[Cl:26]

Participants

3

Reactant 2

HCID 226481625-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carbaldehydeHCID 698499071-Allyl 2-tert-butyl piperazine-1,2-dicarboxylate

Product 1

HCID 698511001-Allyl 2-tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}piperazine-1,2-dicarboxylate

Procedure

The 1-allyl 2-tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}piperazine-1,2-dicarboxylate was prepared from 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carbaldehyde (INTERMEDIATE AAA1) and 1-allyloxycarbonyl-2-t-butyloxycarbonyl piperazine as described in EXAMPLE AAA1, STEP A. 1H NMR (CDCl3, 500 MHz): 1.34 (s, 9H), 1.92 (m, 1H), 2.26 (m, 1H), 2.70 (m, 1H), 3.12 (m, 1H), 3.30 (m, 3H), 3.50 (m, 1H), 3.83 (m, 1H), 4.34 (abq, 2H, J=14.4 Hz), 4.54 (m, 1H), 4.62 (brs, 2H), 5.03 (s, 1H), 5.16-5.36 (m, 2H), 5.93 (brs, 1H), 6.11 (s, 1H), 6.85 (d, 1H, J=10.1 Hz), 7.32-7.56 (m, 7H). MS (API-ES+): 687 (M+H).

Sources & evidence

ORD record
ord-8e4c6c662ed0448eb62adbe280e63e0e
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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