5-(Aminomethyl)-2-(trifluoromethyl)pyridine → 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-((6-(trifluoromethyl)pyridin-3-yl)methyl)thiophene-2-carboxamide

HRID 560885Notes

Reaction equation

HRID 560885 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.[F:48][C:49]([F:59])([F:58])[C:50]1[N:55]=[CH:54][C:53]([CH2:56][NH2:57])=[CH:52][CH:51]=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:57][CH2:56][C:53]4[CH:54]=[N:55][C:50]([C:49]([F:59])([F:48])[F:58])=[CH:51][CH:52]=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 27377185-(Aminomethyl)-2-(trifluoromethyl)pyridineHCID 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 250966935-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-((6-(trifluoromethyl)pyridin-3-yl)methyl)thiophene-2-carboxamideYield 63%

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 (6-(trifluoromethyl)pyridin-3-yl)methanamine, the title compound was obtained as a colorless solid in 63% yield: 1H NMR (300 MHz, CDCl3) δ 8.70 (s, 1H), 7.89 (d, J=8.0 Hz, 1H), 7.65 (d, J=8.0 Hz, 1H), 7.30-7.23 (m, 2H), 7.08-6.99 (m, 2H), 6.20 (t, J=5.8 Hz, 1H), 6.09 (s, 1H), 4.65 (d, J=5.8 Hz, 2H), 4.43 (s, 2H), 3.85-3.77 (m, 2H), 3.49-3.40 (m, 2H), 2.49 (s, 3H): MS (ES+) m/z 493.2 (M+1).

Sources & evidence

ORD record
ord-c8f9b42e2b7f4647a3a9845b1cab7e61
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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