4-Bromoaniline → 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea

HRID 715786Notes

Reaction equation

HRID 715786 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:36]=[CH:35][N:34]3[CH:37]=[CH:38][N:39]=[C:33]3[CH:32]=2)=[O:28])=[CH:22][CH:21]=1.BrC1C=CC(N)=CC=1>>[N:39]1[CH:38]=[CH:37][N:34]2[CH:35]=[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][C:33]=12

Participants

4

Reactant 3

HCID 78074-BromoanilineHCID 27593921-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 867019581-(4-Bromophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea

Product 1

HCID 867019601-(imidazo[1,2-a]pyridin-7-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-7-ylmethyl)urea for 4-bromoaniline. 1H NMR (300 MHz, DMSO-d6) δ 8.62 (s, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 8.04 (d, J=0.8 Hz, 1H), 7.90-7.86 (m, 1H), 7.76 (d, J=0.8 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.46-7.35 (m, 5H), 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), 4.04 (t, J=6.9 Hz, 2H), 1.91-1.73 (m, 2H), 1.26-1.05 (m, 1H), 0.85 (t, J=7.4 Hz, 3H); MS (ESI(+)) m/e 375 (M+H)+.

Sources & evidence

ORD record
ord-f68aee6489ef436e95f4ecdc4e38da37
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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