3-Pyridinemethanamine → 2-(3-((5-(difluoromethyl)furan-2-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 560676Notes

Reaction equation

HRID 560676 reaction equation
C(N1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O)C1C=CC=CC=1.[F:23][CH:24]([F:46])[C:25]1[O:29][C:28]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:37][C:38]([C:42]([OH:44])=O)=[C:39]([CH3:41])[N:40]=3)[C:32]2=[O:45])=[CH:27][CH:26]=1.[NH2:47][CH2:48][C:49]1[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=1>>[F:23][CH:24]([F:46])[C:25]1[O:29][C:28]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:37][C:38]([C:42]([NH:47][CH2:48][C:49]4[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=4)=[O:44])=[C:39]([CH3:41])[N:40]=3)[C:32]2=[O:45])=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 58031550HCID 58031550, compound

Product 1

HCID 594812002-(3-((5-(difluoromethyl)furan-2-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 59%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 2-(3-((5-(difluoromethyl)furan-2-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a white powder in 59% yield: mp 142-143° C. (diethyl ether): 1H NMR (300 MHz, CDCl3) δ 8.60-8.53 (m, 1H), 8.51-8.44 (m, 1H), 7.72-7.62 (m, 1H), 7.28-7.19 (m, 1H), 6.59-6.57 (m, 1H), 6.54 (t, JH-F=54.2 Hz, 1H), 6.33-6.59 (m, 1H), 4.56 (d, J=5.8 Hz, 2H), 4.46 (s, 2H), 4.10-4.03 (m, 2H), 3.61-3.53 (m, 2H), 2.57 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.6, 157.2, 155.1, 153.5, 151.4, 149.2, 148.8, 135.6, 133.9, 123.6, 117.1, 111.3, 109.7, 108.1, 105.0, 42.3, 42.0, 41.3, 40.4, 17.2; MS (ES+) m/z 448.3 (M+1).

Sources & evidence

ORD record
ord-791270ce7c504e31984fbb756d8674b3
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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