3-Pyridinemethanamine → HCID 25095676, compound

HRID 560671Notes

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]=CC=CC=1.CC1N=C(N2CCN(CCC)C2=O)SC=1C(O)=O.[NH2:41][CH2:42][C:43]1[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=1>>[CH3:18][C:16]1[N:17]=[C:13]([N:10]2[CH2:11][CH2:12][N:8]([CH2:1][CH2:2][CH3:7])[C:9]2=[O:22])[S:14][C:15]=1[C:19]([NH:41][CH2:42][C:43]1[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=1)=[O:21]

Participants

Reactant 3

HCID 310183-Pyridinemethanamine

HCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

HCID 58031629HCID 58031629, compound

Product 1

HCID 25095676HCID 25095676, compoundYield 46%

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-propylimidazolidin-1-yl)thiazole-5-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a white powder in 46% yield: mp 109-111° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.52-8.42 (m, 2H), 7.63 (d, J=7.8 Hz, 1H), 7.24-7.17 (m, 1H), 6.54 (t, J=6.0 Hz, 1H), 4.52 (d, J=6.0 Hz, 2H), 4.05-4.00 (m, 2H), 3.55-3.49 (m, 2H), 3.20 (t, J=7.5 Hz, 2H), 2.60 (s, 3H), 1.59-1.49 (m, 2H), 0.85 (t, J=7.5 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 162.8, 157.5, 155.4, 153.5, 149.1, 148.6, 135.6, 134.1, 123.6, 116.7, 45.4, 42.1, 42.0, 41.2, 20.5, 17.2, 11.1; MS (ES+) m/z 360.3 (M+1).

Sources & evidence

ORD record: ord-eabaede72681427e979793093cba41bd
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063084B2

Reaction notes

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