3-((1H-imidazol-1-yl)methyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine → Ethyl 1-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-3-(furan-2-yl)-1H-pyrazole-5-carboxylate

HRID 455023Notes

Reaction equation

HRID 455023 reaction equation
N1(CC2N3C=C(C)C=CC3=NC=2C2C=CC(C)=CC=2)C=CN=C1.Cl.Cl[CH2:26][C:27]1[N:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]2=[N:29][C:28]=1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1.[O:43]1[CH:47]=[CH:46][CH:45]=[C:44]1[C:48]1[NH:52][N:51]=[C:50]([C:53]([O:55][CH2:56][CH3:57])=[O:54])[CH:49]=1>>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([C:28]2[N:29]=[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]3[C:27]=2[CH2:26][N:51]2[C:50]([C:53]([O:55][CH2:56][CH3:57])=[O:54])=[CH:49][C:48]([C:44]3[O:43][CH:47]=[CH:46][CH:45]=3)=[N:52]2)=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 583370713-((1H-imidazol-1-yl)methyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridineHCID 670287193-(Chloromethyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine hydrochlorideHCID 178468634ethyl 3-(furan-2-yl)-1H-pyrazole-5-carboxylate

Product 1

HCID 67029128Ethyl 1-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-3-(furan-2-yl)-1H-pyrazole-5-carboxylate

Procedure

The title compound was prepared according to Method A and the experimentals described for compound 1 from 3-(chloromethyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine hydrochloride and ethyl 5-(furan-2-yl)-1H-pyrazole-3-carboxylate. The regioisomers were separated silica gel chromatography. Compound 30: M/e+ 447 for C24H20ClN4O3 (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8 7.93 (d, J=6.2 Hz, 1H), 7.67 (d, J=7.7 Hz, 2H), 7.56 (d, J=9.1 Hz, 1H), 7.34 (d, J=7.7 Hz, 2H), 7.25 (d, J=2.9 Hz, 1H), 7.17 (m, 1H), 6.98 (s, 1H), 6.81 (t, J=6.6 Hz, 1H), 6.62 (s, 1H), 6.09 (s, 1H), 4.40 (m, 4H), 1.39 (t, J=6.9 Hz, 3H) ppm; Compound 31: M/e+ 447 for C24H20ClN4O3 (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8.37 (d, J=6.9 Hz, 1H), 7.90 (d, J=8.4 Hz, 2H), 7.65 (d, J=9.1 Hz, 1H), 7.42 (m, 3H), 7.24 (m, 1H), 7.09 (s, 1H), 6.84 (td, J=6.6, 1.1 Hz, 1H), 6.58 (d, J=3.3 Hz, 1H), 6.40 (dd, J=3.3, 1.8 Hz, 1H), 6.15 (s, 2H), 4.36 (q, J=7.3 Hz, 2H), 1.39 (t, J=7.3 Hz, 3H) ppm.

Workup

  1. customThe regioisomers were separated silica gel chromatography

Sources & evidence

ORD record
ord-df81f325a0cc4c4ca6cbfe48d0518962
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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