3-Pyridinemethanamine → HCID 59481221, compound

HRID 2067444Notes

Reaction equation

HRID 2067444 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]1C=CC=CC=1.C(N1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O)C.[NH2:40][CH2:41][C:42]1[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=1>>[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C:13]2[S:14][C:15]([C:19]([NH:40][CH2:41][C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)=[O:21])=[C:16]([CH3:18])[N:17]=2)[C:9]1=[O:22])[CH3:2]

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 58031478HCID 58031478, compound

Product 1

HCID 59481221HCID 59481221, compoundYield 16%

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-ethyl-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 16% yield: mp 163-164° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.56-8.48 (m, 2H), 7.66 (d, J=7.8 Hz, 1H), 7.28-7.17 (m, 1H), 6.23 (t, J=5.7 Hz, 1H), 4.55 (d, J=5.7 Hz, 2H), 4.12-4.03 (m, 2H), 3.58-3.53 (m, 2H), 3.35 (q, J=7.2 Hz, 2H), 2.58 (s, 3H), 1.18 (t, J=7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 162.7, 157.5, 155.1, 153.6, 149.2, 148.8, 135.6, 133.9, 123.6, 116.6, 42.0, 41.5, 41.3, 38.5, 17.2, 12.5; MS (ES+) m/z 346.3 (M+1).

Sources & evidence

ORD record
ord-5b156f568b794a07ab8a8c2bbe45084e
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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