2-(Aminomethyl)-5-methylpyrazine → 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((5-methylpyrazin-2-yl)methyl)isonicotinamide

HRID 714354Notes

Reaction equation

HRID 714354 reaction equation
O1C=C(CN)N=C1.[CH3:8][C:9]1[N:10]=[CH:11][C:12]([CH2:15][NH2:16])=[N:13][CH:14]=1.[F:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][N:23]2[CH2:27][CH2:26][N:25]([C:28]3[CH:29]=[C:30]([CH:34]=[CH:35][N:36]=3)[C:31](O)=[O:32])[C:24]2=[O:37])=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][N:23]2[CH2:27][CH2:26][N:25]([C:28]3[CH:29]=[C:30]([CH:34]=[CH:35][N:36]=3)[C:31]([NH:16][CH2:15][C:12]3[CH:11]=[N:10][C:9]([CH3:8])=[CH:14][N:13]=3)=[O:32])[C:24]2=[O:37])=[CH:38][CH:39]=1

Participants

4

Reactant 3

HCID 27564962-(Aminomethyl)-5-methylpyrazineHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 445553042-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((5-methylpyrazin-2-yl)methyl)isonicotinamideYield 39%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with (5-methylpyrazin-2-yl)methanamine to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((5-methylpyrazin-2-yl)methyl)isonicotinamide was obtained as a colorless solid in 39% yield: mp 169-171° C.; 1H NMR (300 MHz, CDCl3) δ 8.65 (s, 1H), 8.52 (d, J=0.9 Hz, 1H), 8.39-8.35 (m, 2H), 7.46 (br s, 1H), 7.39-7.37 (m, 1H), 7.29-7.24 (m, 2H), 7.05-6.99 (m, 2H), 4.74 (d, J=5.1 Hz, 2H), 4.44 (s, 2H), 4.04 (t, J=8.1 Hz, 2H), 3.37 (t, J=8.1 Hz, 2H), 2.54 (s, 3H); MS (ES+) m/z 421.1 (M+1).

Sources & evidence

ORD record
ord-cc3e93d1295a482aae82cbc19fabd3f3
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

Loading…