3-Pyridinemethanamine → 5-(3-(4-carbamoylbenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-(pyridin-3-ylmethyl)thiophene-2-carboxamide

HRID 560881Notes

Reaction equation

HRID 560881 reaction equation
CC1C=C(N2CCN(CCOC3C=CC=CC=3)C2=O)SC=1C(O)=O.[C:25]([C:28]1[CH:49]=[CH:48][C:31]([CH2:32][N:33]2[CH2:37][CH2:36][N:35]([C:38]3[S:42][C:41]([C:43]([OH:45])=O)=[C:40]([CH3:46])[CH:39]=3)[C:34]2=[O:47])=[CH:30][CH:29]=1)(=[O:27])[NH2:26].[NH2:50][CH2:51][C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1>>[C:25]([C:28]1[CH:49]=[CH:48][C:31]([CH2:32][N:33]2[CH2:37][CH2:36][N:35]([C:38]3[S:42][C:41]([C:43]([NH:50][CH2:51][C:52]4[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=4)=[O:45])=[C:40]([CH3:46])[CH:39]=3)[C:34]2=[O:47])=[CH:30][CH:29]=1)(=[O:27])[NH2:26]

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 580314563-Methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acidHCID 580316105-(3-(4-Carbamoylbenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid

Product 1

HCID 250959275-(3-(4-carbamoylbenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-(pyridin-3-ylmethyl)thiophene-2-carboxamideYield 71%

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-carbamoylbenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a cream solid in 71% yield: mp 188° C. (dec.): 1H NMR (300 MHz, DMSO-6) δ 8.53 (s, 1H), 8.45 (d. J=4.0 Hz, 1H), 8.31, (t, J=5.8 Hz, 1H), 7.97 (s, 1H), 7.86 (d, J=8.0 Hz, 2H), 7.71 (d, J=7.8 Hz, 1H), 7.42-7.32 (m, 4H), 6.24 (s, 1H), 4.44 (s, 2H), 4.39 (d, J=5.8 Hz, 2H), 3.84 (t, J=7.8 Hz, 2H), 3.45 (t, J=7.8 Hz, 2H), 2.37 (s, 3H): 13C NMR (75 MHz, DMSO-d6) δ 167.5, 162.9, 155.5, 148.8, 147.8, 140.0, 139.0, 135.4, 135.0, 133.4, 127.7, 127.4, 123.3, 119.9, 112.0, 46.8, 42.5, 41.5, 15.7: MS (ES+) m/z 450.4 (M+1).

Sources & evidence

ORD record
ord-813e266404ee47e98586be7cd12bc64c
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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