Benzylamine → N-benzyl-4-((3-(4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzamide

HRID 2067401Notes

Reaction equation

HRID 2067401 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C:13]2[S:14][C:15](C(O)=O)=[C:16]([CH3:18])[N:17]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1N=C(N2CC[N:31]([CH2:34][C:35]3[CH:43]=[CH:42][C:38](C(O)=O)=[CH:37][CH:36]=3)[C:30]2=[O:44])SC=1.C(N)C1C=CC=CC=1>>[CH2:34]([NH:31][C:30](=[O:44])[C:5]1[CH:4]=[CH:3][C:2]([CH2:1][N:8]2[CH2:12][CH2:11][N:10]([C:13]3[S:14][CH:15]=[C:16]([CH3:18])[N:17]=3)[C:9]2=[O:22])=[CH:7][CH:6]=1)[C:35]1[CH:43]=[CH:42][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 580315034-((3-(4-Methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acid

Product 1

HCID 59481215N-benzyl-4-((3-(4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzamideYield 60%

Procedure

Following the procedure as describe in Example 8, making variations as required to replace 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 4-((3-(4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acid to react with benzylamine, the title compound was obtained as a white powder in 60% yield: mp 185-186° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.76 (d, J=9.0 Hz, 2H), 7.30-7.28 (m, 6H), 6.73 (t, J=6.0 Hz, 2H), 6.41 (s, 1H), 4.59 (d, J=6.0 Hz, 2H), 4.44 (s, 2H), 4.05-4.00 (m, 2H), 3.40-3.35 (m, 2H), 2.29 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 166.8, 158.7, 155.9, 147.2, 139.6, 138.2, 134.0, 128.7, 128.3, 127.9, 127.6, 127.5, 106.9, 47.6, 44.0, 42.3, 41.9, 17.3; MS (ES+) m/z 407.2 (M+1).

Sources & evidence

ORD record
ord-14e559d1616d4edf8ad70172a8460793
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

Loading…