2,4-Difluorophenylboronic acid → 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-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[C:2]1[CH:11]=[C:10]([CH2:12][N:13]2[CH2:18][CH:17]3[CH2:19][CH:14]2[CH2:15][N:16]3[CH:20]([CH3:22])[CH3:21])[CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)[C:6](=[O:31])[N:7]2[C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:30].[F:41][C:42]1[CH:47]=[C:46]([F:48])[CH:45]=[CH:44][C:43]=1B(O)O>>[Cl:30][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([Cl:29])[C:23]=1[N:7]1[C:8]2[C:3](=[C:2]([C:45]3[CH:44]=[CH:43][C:42]([F:41])=[CH:47][C:46]=3[F:48])[CH:11]=[C:10]([CH2:12][N:13]3[CH2:18][CH:17]4[CH2:19][CH:14]3[CH2:15][N:16]4[CH:20]([CH3:21])[CH3:22])[CH:9]=2)[CH2:4][N:5]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)[C:6]1=[O:31]Participants
Reactant 2
Product 1
Procedure
The 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-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)-7-[(5-isopropyl-2,5-diazabicyclo[2.2.1]hept-2-yl)methyl]-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one (EXAMPLE AAA16, STEP C) and 2,4-difluorobenzene boronic acid as described in EXAMPLE AAA16, STEP D. 1H NMR (CDCl3, 500 MHz): δ 1.03 (s, 3H), 1.08 (s, 3H), 1.59 (brs, 2H), 2.40 (m, 2H), 2.56 (brs, 1H), 2.83 (m, 1H), 2.90 (brs, 1H), 3.15 (s, 1H), 3.58 (abq, 3H, J=14.5 Hz), 3.81 (s, 3H), 4.20 (brs, 2H), 4.58 (brs, 2H), 6.23 (s, 1H), 6.85 (m, 3H), 6.91 (m, 2H), 7.14 (q, 1H, J=7.1 Hz), 7.23 (d, 2H, J=8.5 Hz), 7.39 (t, 1H, J=8.0 Hz), 7.54 (d, 2H, J=8.1 Hz). MS (API-ES+): 677 (M+H).
Sources & evidence
- ORD record
- ord-d9d4bf5a7df347ba91cff6d0c2337d04
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809199B2
Reaction notes
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