3-Pyridinemethanamine → HCID 59481188, compound

HRID 560673Notes

Reaction equation

HRID 560673 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]=CC=1.CC1N=C(N2CCN(CCCCC)C2=O)SC=1C(O)=O.[NH2:43][CH2:44][C:45]1[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=1>>[CH3:18][C:16]1[N:17]=[C:13]([N:10]2[CH2:11][CH2:12][N:8]([CH2:1][CH2:2][CH2:7][CH2:6][CH3:5])[C:9]2=[O:22])[S:14][C:15]=1[C:19]([NH:43][CH2:44][C:45]1[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=1)=[O:21]

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 58031527HCID 58031527, compound

Product 1

HCID 59481188HCID 59481188, compoundYield 40%

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 4-methyl-2-(2-oxo-3-pentylimidazolidin-1-yl)thiazole-5-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a white powder in 40% yield: mp 102-103° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.54-8.43 (m, 2H), 7.63 (d, J=7.5 Hz, 1H), 7.21-7.17 (m, 1H), 6.50 (br s, 1H), 4.54 (J=5.8 Hz, 2H), 4.05-3.97 (m, 2H), 3.55-3.47 (m, 2H), 3.26-3.14 (m, 2H), 2.55 (s, 3H), 1.52-1.46 (m, 2H), 1.30-1.20 (m, 4H), 0.84 (t, J=6.6 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 162.7, 157.5, 155.4, 153.6, 149.2, 148.8, 135.5, 134.0, 123.6, 116.6, 43.8, 42.1, 42.0, 41.3, 28.8, 26.9, 22.3, 17.3, 14.0; MS (ES+) m/z 388.3 (M+1).

Sources & evidence

ORD record
ord-b8ea0563428f450e976755de4a785ef6
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

Loading…