4-Bromoaniline → 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea
Reaction equation
[CH2:1]([N:4]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[N:5]1)[CH2:2][CH3:3].Br[C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][N:33]3[CH:36]=[CH:37][N:38]=[C:32]3[CH:31]=2)=[O:27])=[CH:21][CH:20]=1.Br[C:40]1C=CC(N)=CC=1>>[N:38]1[CH:37]=[CH:36][N:33]2[CH:34]=[CH:35][C:30]([CH2:29][NH:28][C:26]([NH:25][C:22]3[CH:23]=[CH:24][C:19]([C:7]4[CH:6]=[N:5][N:4]([CH2:1][CH:2]([CH3:3])[CH3:40])[CH:8]=4)=[CH:20][CH:21]=3)=[O:27])=[CH:31][C:32]=12Participants
4
Procedure
The title compound was prepared as described in Example 51A, substituting substituting 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.62 (s, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 8.02 (d, J=0.8 Hz, 1H), 7.88 (dd, J=1.2, 0.7 Hz, 1H), 7.77 (d, J=0.8 Hz, 1H), 7.54-7.34 (m, 6H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.69 (t, J=6.0 Hz, 1H), 4.34 (d, J=5.9 Hz, 2H), 3.90 (d, J=7.1 Hz, 2H), 2.21-2.04 (m, 1H), 0.86 (d, J=6.7 Hz, 6H).
Sources & evidence
- ORD record
- ord-00f4a64b03494487816f53ba61220906
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193723B2
Reaction notes
Loading…