(1-methyl-1H-imidazol-4-yl)methanamine → 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((1-methyl-1H-imidazol-4-yl)methyl)isonicotinamide

HRID 714357Notes

Reaction equation

HRID 714357 reaction equation
O1C=C(CN)N=C1.[CH3:8][N:9]1[CH:13]=[C:12]([CH2:14][NH2:15])[N:11]=[CH:10]1.[F:16][C:17]1[CH:38]=[CH:37][C:20]([CH2:21][N:22]2[CH2:26][CH2:25][N:24]([C:27]3[CH:28]=[C:29]([CH:33]=[CH:34][N:35]=3)[C:30](O)=[O:31])[C:23]2=[O:36])=[CH:19][CH:18]=1>>[F:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][N:22]2[CH2:26][CH2:25][N:24]([C:27]3[CH:28]=[C:29]([CH:33]=[CH:34][N:35]=3)[C:30]([NH:15][CH2:14][C:12]3[N:11]=[CH:10][N:9]([CH3:8])[CH:13]=3)=[O:31])[C:23]2=[O:36])=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 2795114(1-methyl-1H-imidazol-4-yl)methanamineHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 445553072-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((1-methyl-1H-imidazol-4-yl)methyl)isonicotinamideYield 52%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with (1-methyl-1H-imidazol-4-yl)methanamine to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((1-methyl-1H-imidazol-4-yl)methyl)isonicotinamide was obtained as a colorless solid in 52% yield: mp 174-176° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.01 (t, J=5.6 Hz, 1H), 8.57 (s, 1H), 8.34 (d, J=5.1 Hz, 1H), 7.45 (s, 1H), 7.35-7.31 (m, 3H), 7.19-7.12 (m, 2H), 6.93 (s, 1H), 4.38 (s, 2H), 4.28 (d, J=5.7 Hz, 2H), 3.93 (t, J=8.1 Hz, 2H), 3.56 (s, 3H), 3.34 (t, J=8.1 Hz, 2H); MS (ES+) m/z 409.1 (M+1).

Sources & evidence

ORD record
ord-4f33ccc8ab384d9c917d0c8c8af085b0
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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