Methylamine → 3-((6-fluoro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-N-methyl-1,2,4-oxadiazole-5-carboxamide

HRID 455138Notes

Reaction equation

HRID 455138 reaction equation
ClC1C=CC([C:8]2[N:9]=C3C=CC=CN3C=2CC2N=C(C(NN)=O)ON=2)=CC=1.[F:27][C:28]1[CH:29]=[CH:30][C:31]2[N:32]([C:34]([CH2:44][C:45]3[N:49]=[C:48]([C:50]([O:52]CC)=O)[O:47][N:46]=3)=[C:35]([C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)[N:36]=2)[CH:33]=1.CN>>[F:27][C:28]1[CH:29]=[CH:30][C:31]2[N:32]([C:34]([CH2:44][C:45]3[N:49]=[C:48]([C:50]([NH:9][CH3:8])=[O:52])[O:47][N:46]=3)=[C:35]([C:37]3[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=3)[N:36]=2)[CH:33]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 670286833-((2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1,2,4-oxadiazole-5-carbohydrazideHCID 67306340Ethyl 3-((6-fluoro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1,2,4-oxadiazole-5-carboxylate

Product 1

HCID 670275303-((6-fluoro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-N-methyl-1,2,4-oxadiazole-5-carboxamide

Procedure

The title compound was prepared in the same fashion as that for compound 215 from ethyl 3-((6-fluoro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1,2,4-oxadiazole-5-carboxylate and methylamine. m/e+=370 (M+H−). 1H NMR (400 MHz, in DMSO-d6): δ 9.23 (H, D, brd, NH), δ 8.66-8.65 (1H, D, dd, J=5.2, 2.0 Hz, ArH), δ 7.81-7.78 (2H, D, m, ArH), δ 7.45-7.40 (1H, D, dd, J=9.6, 5.2 Hz, ArH), δ 7.32-7.28 (2H, D, m, ArH), δ 4.72 (2H, D, s, CH2), and 2.76 (3H, D, s, CH3).

Sources & evidence

ORD record
ord-bddb66627c2c49b7a3e9909f14d1c975
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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