1-Benzothiophen-2-ylmethylamine → N-(benzo[b]thiophen-2-ylmethyl)-5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxamide

HRID 560888Notes

Reaction equation

HRID 560888 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]([OH:43])=O)=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:28][CH:27]=1.[S:48]1[C:52]([CH2:53][NH2:54])=[CH:51][C:50]2[CH:55]=[CH:56][CH:57]=[CH:58][C:49]1=2>>[S:48]1[C:52]([CH2:53][NH:54][C:41]([C:39]2[S:40][C:36]([N:33]3[CH2:34][CH2:35][N:31]([CH2:30][C:29]4[CH:46]=[CH:47][C:26]([F:25])=[CH:27][CH:28]=4)[C:32]3=[O:45])=[CH:37][C:38]=2[CH3:44])=[O:43])=[CH:51][C:50]2[CH:55]=[CH:56][CH:57]=[CH:58][C:49]1=2

Participants

4

Reactant 3

HCID 2370741-Benzothiophen-2-ylmethylamineHCID 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 59481216N-(benzo[b]thiophen-2-ylmethyl)-5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxamideYield 78%

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 benzo[b]thiophen-2-ylmethanamine, the title compound was obtained as a colorless solid in 78% yield: 1H NMR (300 MHz, CDCl3) δ 7.78 (d, J=7.6 Hz, 1H), 7.70 (d, J=7.6 Hz, 1H), 7.36-7.22 (m, 5H), 7.08-6.99 (m, 2 H), 6.14 (t, J=5.4 Hz, 1H), 6.10 (s, 1H), 4.82 (d, J=5.4 Hz, 2H), 4.42 (s, 2H), 3.83-3.74 (m, 2H), 3.47-3.38 (m, 2H), 2.51 (s, 3H); MS (ES+) m/z 480.2 (M+1).

Sources & evidence

ORD record
ord-caf0a50e20d7481e9bc86c9935d4591d
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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