(3-Methylthiophen-2-yl)methanamine → 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-((3-methylthiophen-2-yl)methyl)thiophene-2-carboxamide

HRID 560886Notes

Reaction equation

HRID 560886 reaction equation
CC1C=C(N2CCN(CCOC3C=CC=CC=3)C2=O)SC=1C(O)=O.[F:25][C:26]1[CH:47]=[CH:46][C:29]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:40][C:39]([C:41](O)=[O:42])=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:28][CH:27]=1.[CH3:48][C:49]1[CH:53]=[CH:52][S:51][C:50]=1[CH2:54][NH2:55]>>[F:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:40][C:39]([C:41]([NH:55][CH2:54][C:50]4[S:51][CH:52]=[CH:53][C:49]=4[CH3:48])=[O:42])=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:46][CH:47]=1

Participants

4

Reactant 3

HCID 2798756(3-Methylthiophen-2-yl)methanamineHCID 580314563-Methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acidHCID 580314655-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid

Product 1

HCID 594812105-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-((3-methylthiophen-2-yl)methyl)thiophene-2-carboxamideYield 73%

Procedure

Following the procedures as described in Example 55, making variations as required to replace 3-methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acid with 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid to react with (3-methylthiophen-2-yl)methanamine, the title compound was obtained as a colorless solid in 73% yield: 1H NMR (300 MHz, CDCl3) δ 7.30-7.23 (m, 2H), 7.13 (d, J=5.0 Hz, 1H), 7.08-6.99 (m, 2H), 6.82 (d, J=5.0 Hz, 1H), 6.08 (s, 1H), 5.83 (br s, 1H), 4.65 (d, J=5.0 Hz, 2H), 4.42 (s, 2H), 3.83-3.74 (m, 2H), 3.47-3.39 (m, 2H), 2.49 (5, 3H), 2.24 (s, 3H): MS (ES+) m/z 444.2 (M+1).

Sources & evidence

ORD record
ord-542f035873c349a3842cdc1d3a794f39
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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