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

HRID 2067402Notes

Reaction equation

HRID 2067402 reaction equation
C(N)C1C=CC=CC=1.[NH2:9][C:10]1[S:11][CH:12]=[C:13]([CH3:15])[N:14]=1.[CH3:16][C:17]1[N:18]=[C:19]([N:22]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=3)[C:23]2=[O:37])[S:20][CH:21]=1>>[CH3:15][C:13]1[N:14]=[C:10]([NH:9][C:32](=[O:33])[C:31]2[CH:35]=[CH:36][C:28]([CH2:27][N:24]3[CH2:25][CH2:26][N:22]([C:19]4[S:20][CH:21]=[C:17]([CH3:16])[N:18]=4)[C:23]3=[O:37])=[CH:29][CH:30]=2)[S:11][CH:12]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 741432-Amino-4-methylthiazoleHCID 580315034-((3-(4-Methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acid

Product 1

HCID 59481270N-(4-methylthiazol-2-yl)-4-((3-(4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzamideYield 41%

Procedure

Following the procedure as describe in Example 8, making variations as required to replace benzylamine with 2-amino-4-methylthiazole to react with 4-((3-(4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acid, the title compound was obtained as a white powder in 41% yield: mp 197-198° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 11.54 (br s, 1H), 7.87 (d, J=6.0 Hz, 2H), 7.37 (d, J=6.0 Hz, 2H), 6.52 (s, 1H), 6.43 (s, 1H), 4.53 (s, 2H), 4.11-4.06 (m, 2H), 3.46-3.41 (m, 2H), 2.30 (s, 3H), 1.97 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 164.8, 158.9, 158.7, 156.0, 147.3, 146.9, 141.2, 132.1, 128.5, 128.3, 108.6, 106.9, 47.7, 42.3, 42.0, 17.3, 16.6; MS (ES+) m/z 414.1 (M+1).

Sources & evidence

ORD record
ord-d12e27768d6d42db82326704013ff718
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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