4-Bromoaniline → 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea

HRID 715776Notes

Reaction equation

HRID 715776 reaction equation
[CH2:1]([N:5]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[N:6]1)[CH:2]([CH3:4])C.Br[C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][CH2:30][C:31]2[CH:32]=[CH:33][C:34]3[N:35]([CH:37]=[CH:38][N:39]=3)[CH:36]=2)=[O:28])=[CH:22][CH:21]=1.BrC1C=CC(N)=CC=1>>[N:39]1[CH:38]=[CH:37][N:35]2[CH:36]=[C:31]([CH2:30][NH:29][C:27]([NH:26][C:23]3[CH:24]=[CH:25][C:20]([C:8]4[CH:7]=[N:6][N:5]([CH2:1][CH2:2][CH3:4])[CH:9]=4)=[CH:21][CH:22]=3)=[O:28])[CH:32]=[CH:33][C:34]=12

Participants

4

Reactant 3

HCID 78074-BromoanilineHCID 27593921-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 867019491-(4-Bromophenyl)-3-(imidazo[1,2-a]pyridin-6-ylmethyl)urea

Product 1

HCID 726995271-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea

Procedure

The title compound was prepared as described in Example 51A, substituting 1-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-6-ylmethyl)urea for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.59 (s, 1H), 8.44 (s, 1H), 8.04 (s, 1H), 7.95 (s, 1H), 7.76 (s, 1H), 7.57-7.50 (m, 2H), 7.48-7.32 (m, 4H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 6.65 (t, J=5.9 Hz, 1H), 4.30 (d, J=5.8 Hz, 2H), 4.04 (t, J=6.9 Hz, 2H), 1.87-1.73 (m, 2H), 0.84 (t, J=7.3 Hz, 3H); MS (ESI(+)) m/e 375 (M+H)+.

Sources & evidence

ORD record
ord-6a3a7985bd8f42509624294507614892
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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