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

HRID 714358Notes

Reaction equation

HRID 714358 reaction equation
O1C=C(CN)N=C1.[CH3:8][N:9]1[CH:13]=[CH:12][C:11]([CH2:14][NH2:15])=[N: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:11]3[CH:12]=[CH:13][N:9]([CH3:8])[N:10]=3)=[O:31])[C:23]2=[O:36])=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 7019419(1-Methylpyrazol-3-yl)methanamineHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 445527432-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((1-methyl-1H-pyrazol-3-yl)methyl)isonicotinamideYield 30%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with (1-methyl-1H-pyrazol-3-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-pyrazol-3-yl)methyl)isonicotinamide was obtained as a colorless solid in 30% yield: mp 79-81° C.; 1H NMR (300 MHz, CDCl3) δ 8.57 (s, 1H), 8.33 (d, J=5.1 Hz, 1H), 7.37 (dd, J=5.1 Hz, 1.2 Hz, 1H), 7.27-7.22 (m, 3H), 7.03-6.91 (m, 3H), 6.19 (d, J=2.1 Hz, 1H), 4.60 (d, J=5.1 Hz, 2H), 4.41 (s, 2H), 4.02 (t, J=8.1 Hz, 2H), 3.84 (s, 3H), 3.34 (t, J=8.1 Hz, 2H); MS (ES+) m/z 408.8 (M+1).

Sources & evidence

ORD record
ord-7aa39984a4e34ccc85e9e7805b6f1a0f
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

Loading…