2-Isopropyl-2,5-diazabicyclo[2.2.1]heptane → 5-bromo-1-(2,6-dichlorophenyl)-7-[(5-isopropyl-2,5-diazabicyclo[2.2.1]hept-2-yl)methyl]-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one
Reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([CH:12]=O)[CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[C:6](=[O:22])[N:7]2[C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21].[CH:32]([N:35]1[CH2:40][CH:39]2[CH2:41][CH:36]1[CH2:37][NH:38]2)([CH3:34])[CH3:33]>>[Br:1][C:2]1[CH:11]=[C:10]([CH2:12][N:38]2[CH2:37][CH:36]3[CH2:41][CH:39]2[CH2:40][N:35]3[CH:32]([CH3:34])[CH3:33])[CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[C:6](=[O:22])[N:7]2[C:14]1[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=1[Cl:20]Participants
Reactant 2
Product 1
Procedure
The 5-bromo-1-(2,6-dichlorophenyl)-7-[(5-isopropyl-2,5-diazabicyclo[2.2.1]hept-2-yl)methyl]-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one was prepared from 5-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carbaldehyde (EXAMPLE AAA16, STEP B) and 2-isopropyl-2,5-diazabicyclo[2.2.1]heptane (INTERMEDIATE ABA2) as described in EXAMPLE AAA1, STEP A. 1H NMR (CDCl3, 500 MHz): δ 1.15 (brs, 3H), 1.22 (brs, 3H), 1.74 (brs, 1H), 1.90 (brs, 1H), 243 (brs, 2H), 2.72 (brs, 1H), 2.88 (brs, 1H), 3.07 (brs, 1H), 3.16 (s, 2H), 3.53 (abq, 2H, J=14.2 Hz), 3.72 (brs, 1H), 3.83 (s, 3H), 4.48 (s, 2H), 4.68 (s, 2H), 6.05 (s, 1H), 6.91 (d, 2H, J=8.5 Hz), 7.17 (s, 1H), 7.36 (d, 2H, J=8.4 Hz), 7.38 (t, 1H, J=8.0 Hz), 7.52 (d, 2H, J=8.0 Hz). MS (API-ES+): 645 (M+H).
Sources & evidence
- ORD record
- ord-8d2c199e73fc4e78933e1e99ce285da7
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809199B2
Reaction notes
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