5-(Aminomethyl)-1,3-thiazole → 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(thiazol-5-ylmethyl)isonicotinamide

HRID 714353Notes

Reaction equation

HRID 714353 reaction equation
O1C=C(CN)N=C1.[S:8]1[C:12]([CH2:13][NH2:14])=[CH:11][N:10]=[CH:9]1.[F:15][C:16]1[CH:37]=[CH:36][C:19]([CH2:20][N:21]2[CH2:25][CH2:24][N:23]([C:26]3[CH:27]=[C:28]([CH:32]=[CH:33][N:34]=3)[C:29](O)=[O:30])[C:22]2=[O:35])=[CH:18][CH:17]=1>>[F:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][N:21]2[CH2:25][CH2:24][N:23]([C:26]3[CH:27]=[C:28]([CH:32]=[CH:33][N:34]=3)[C:29]([NH:14][CH2:13][C:12]3[S:8][CH:9]=[N:10][CH:11]=3)=[O:30])[C:22]2=[O:35])=[CH:36][CH:37]=1

Participants

4

Reactant 3

HCID 53040775-(Aminomethyl)-1,3-thiazoleHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 445553032-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(thiazol-5-ylmethyl)isonicotinamideYield 43%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with thiazol-5-ylmethanamine to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(thiazol-5-ylmethyl)isonicotinamide was obtained as a colorless solid in 43% yield: mp 148-150° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.39 (t, J=5.7 Hz, 1H), 9.02 (s, 1H), 8.65 (s, 1H), 8.36 (d, J=5.1 Hz, 1H), 7.80 (s, 1H), 7.35-7.29 (m, 3H), 7.19-7.13 (m, 2H), 4.64 (d, J=5.7 Hz, 2H), 4.39 (s, 2H), 3.93 (t, J=8.0 Hz, 2H), 3.34 (t, J=8.0 Hz, 2H); MS (ES+) m/z 412.0 (M+1).

Sources & evidence

ORD record
ord-a1d50ad84d7d479db6673acc6af0b882
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

Loading…