(2-Methylthiazol-4-yl)MethanaMine → 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((2-methylthiazol-4-yl)methyl)isonicotinamide

HRID 714365Notes

Reaction equation

HRID 714365 reaction equation
O1C=C(CN)N=C1.[CH3:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][NH2:15])[N:13]=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:13]=[C:9]([CH3:8])[S:10][CH:11]=3)=[O:31])[C:23]2=[O:36])=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 18467479(2-Methylthiazol-4-yl)MethanaMineHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 445529142-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((2-methylthiazol-4-yl)methyl)isonicotinamideYield 26%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with (2-methylthiazol-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-((2-methylthiazol-4-yl)methyl)isonicotinamide was obtained as a colorless solid in 26% yield: mp 76-78° C.; 1H NMR (300 MHz, CDCl3) δ 8.60 (d, J=0.6 Hz, 1H), 8.34 (d, J=5.7 Hz, 1H), 7.36 (dd, J=5.4, 1.5 Hz, 1H), 7.28-7.24 (m, 2H), 7.05-6.99 (m, 4H), 4.66 (d, J=5.7 Hz, 2H), 4.43 (s, 2H), 4.03 (t, J=8.1 Hz, 2H), 3.36 (t, J=8.1 Hz, 2H), 2.68 (s, 3H); MS (ES+) m/z 425.8 (M+1).

Sources & evidence

ORD record
ord-0aed8a7c292e4b8f8aca34afbf2300c6
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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