3-Pyridinemethanamine → HCID 59481312, compound

HRID 560672Notes

Reaction equation

HRID 560672 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]C=CC=1.C(N1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O)CCC.[NH2:42][CH2:43][C:44]1[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=1>>[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C:13]2[S:14][C:15]([C:19]([NH:42][CH2:43][C:44]3[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=3)=[O:21])=[C:16]([CH3:18])[N:17]=2)[C:9]1=[O:22])[CH2:2][CH2:7][CH3:6]

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 58031429HCID 58031429, compound

Product 1

HCID 59481312HCID 59481312, compoundYield 33%

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-butyl-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 33% yield: mp 109-111° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.55-8.45 (m, 2H), 7.63 (d, J=7.8 Hz, 1H), 7.24-7.19 (m, 1H), 6.45 (br s, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.05-4.00 (m, 2H), 3.55-3.49 (m, 2H), 3.31-3.18 (m, 2H), 2.55 (s, 3H), 1.53-1.20 (m, 4H), 0.88 (t, J=7.5 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, 43.5, 42.1, 42.0, 41.3, 29.3, 19.8, 17.2, 13.6; MS (ES+) m/z 374.3 (M+1).

Sources & evidence

ORD record
ord-e7f4f813c2544f68a08de8244212d1d8
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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