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

HRID 560727Notes

Reaction equation

HRID 560727 reaction equation
CC1C=C(N2CCN(CC3C=CC(C(F)(F)F)=CC=3)C2=O)SC=1C(O)=O.[F:27][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.[NH2:50][CH2:51][C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1>>[F:27][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

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 580314655-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acidHCID 580315813-Methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylic acid

Product 1

HCID 594812595-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-(pyridin-3-ylmethyl)thiophene-2-carboxamideYield 79%

Procedure

Following the procedure as described in Example 15, making variations as required to replace 3-methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)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-(aminomethyl)pyridine, the title compound was obtained as a colorless solid in 79% yield: mp 119-120° C.; 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.52 (d, J=4.7 Hz, 1H), 7.69 (d, J=7.8 Hz, 1H), 7.29-7.23 (m, 3H), 7.06-6.99 (m, 2H), 6.14 (t, J=5.7 Hz, 1H), 6.08 (s, 1H), 4.58 (d, J=5.7 Hz, 2H), 4.42 (s, 2H), 3.83-3.75 (m, 2H), 3.47-3.39 (m, 2H), 2.48 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 163.5, 162.4 (d, JC-F=246.4 Hz), 155.8, 149.2, 148.8, 142.5, 141.7, 135.5, 134.1, 131.7, (d, JC-F=3.1 Hz), 130.0 (d, JC-F=8.2 Hz), 123.6, 119.0, 115.7 (d, JC-F=21.5 Hz), 112.4, 47.4, 42.7, 41.4, 41.2, 16.1; MS (ES+) m/z 425.3 (M+1).

Sources & evidence

ORD record
ord-c069f649b1e242da8bee110d54a68f6f
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

Loading…