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

HRID 560901Notes

Reaction equation

HRID 560901 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[S:53][C:52]([CH2:54][NH2:55])=[CH:51][CH:50]=1>>[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:52]4[S:53][C:49]([CH3:48])=[CH:50][CH:51]=4)=[O:42])=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:46][CH:47]=1

Participants

4

Reactant 3

HCID 4313442(5-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 594811805-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-((5-methylthiophen-2-yl)methyl)thiophene-2-carboxamideYield 41%

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 (5-methylthiophen-2-yl)methanamine, the title compound was obtained as a colorless solid in 41% yield: 1H NMR (300 MHz, CDCl3) δ 7.30-7.23 (m, 2H), 7.07-6.98 (m, 2H), 6.78 (d, J=3.2 Hz, 1H), 6.58 (d, J=3.2 Hz, 1 H), 6.09 (s, 1H), 5.94 (t, J=5.1 Hz, 1H), 4.64 (d, J=5.1 Hz, 2H), 4.42 (s, 2H), 3.83-3.74 (m, 2H), 3.47-3.39 (m, 2H), 2.49 (s, 3H), 2.44 (s, 3H); MS (ES+) m/z 466.2 (M+23).

Sources & evidence

ORD record
ord-86485dc57aa847e3b2cd3dea788e9fb5
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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