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

HRID 560666Notes

Reaction equation

HRID 560666 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C:13]2[S:14][C:15]([C:19]([OH:21])=O)=[C:16]([CH3:18])[N:17]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(CN2CCN(C3SC(C(O)=O)=C(C)N=3)C2=O)CCCCC1.[NH2:45][CH2:46][C:47]1[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=1>>[CH:2]1([CH2:1][N:8]2[CH2:12][CH2:11][N:10]([C:13]3[S:14][C:15]([C:19]([NH:45][CH2:46][C:47]4[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=4)=[O:21])=[C:16]([CH3:18])[N:17]=3)[C:9]2=[O:22])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 580313962-(3-(Cyclohexylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 594811962-(3-(cyclohexylmethyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 52%

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-(cyclohexylmethyl)-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 52% yield: mp 134-136° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.57-8.47 (m, 2H), 7.68 (d, J=7.2 Hz, 1H), 7.27 (s, 1H), 6.31 (br s, 1H), 4.55 (d, J=5.7 Hz, 2H), 4.11-4.03 (m, 2H), 3.57 (m, 2H), 3.09 (d, J=7.2 Hz, 2H), 2.57 (s, 3H), 1.84-1.56 (m, 5H), 1.24-0.84 (m 6H); 13C NMR (75 MHz, CDCl3) δ 162.7, 157.5, 155.6, 153.6, 148.9, 148.5, 135.9, 134.2, 123.7, 116.5, 50.3, 43.0, 42.0, 41.3, 36.0, 30.7, 26.2, 25.6, 17.2; MS (ES+) m/z 414.3 (M+1).

Sources & evidence

ORD record
ord-07f2f6156f564381b4111d6d50cb43fa
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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