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

HRID 560626Notes

Reaction equation

C(N)C1C=CC=CC=1.[F:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1.[CH3:17][C:18]1[N:19]=[C:20]([N:23]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=3)[C:24]2=[O:38])[S:21][CH:22]=1>>[F:9][C:10]1[CH:16]=[CH:15][C:13]([NH:14][C:33](=[O:34])[C:32]2[CH:36]=[CH:37][C:29]([CH2:28][N:25]3[CH2:26][CH2:27][N:23]([C:20]4[S:21][CH:22]=[C:18]([CH3:17])[N:19]=4)[C:24]3=[O:38])=[CH:30][CH:31]=2)=[CH:12][CH:11]=1

Participants

Reactant 3

HCID 7504Benzylamine

HCID 97314-Fluoroaniline

HCID 580315034-((3-(4-Methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acid

Product 1

HCID 58031684N-(4-fluorophenyl)-4-((3-(4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzamideYield 16%

Procedure

Following the procedure as describe in Example 8, making variations as required to replace benzylamine with 4-fluoroaniline 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 16% yield: mp 206-207° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.74 (d, J=7.2 Hz, 2H), 7.52-7.44 (m, 2H), 7.23 (d, J=7.2 Hz, 2H), 6.90-6.85 (m, 2H), 6.33 (s, 1H), 4.37 (s, 2H), 3.95-3.90 (m, 2H), 3.37-3.31 (m, 2H), 2.16 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.0, 155.9, 146.7, 139.5, 134.2, 127.9, 127.8, 122.6, 115.3, 115.1, 106.9, 47.3, 42.2, 41.8, 16.5; MS (ES+) m/z 411.1 (M+1).

Sources & evidence

ORD record: ord-6be28fe9954d473da1b070b47724fa31
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063084B2

Reaction notes

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