2-Aminopyridine → HCID 5273632, compound

HRID 2257785Notes

Reaction equation

HRID 2257785 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][NH:11][C:12]([N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)=[S:13].N[C:20]1[CH:25]=CC=CN=1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][NH:11][C:12]([NH:14][C:15]1[CH:25]=[CH:20][CH:18]=[CH:17][N:16]=1)=[S:13]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 19704106HCID 19704106, compound

Product 1

HCID 5273632HCID 5273632, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(2-[2-methoxyphenyl]ethyl)thiocarbamoyl imidazole (0.52 g, 2 mmol ) and 2-aminopyridine (0.19 g, 2 mmol) in N,N-dimethylformamide (5 mL) was stirred at 90° C. for 4 h, the reaction was cooled to room temperature and the solvent removed in vacuo. The residue was crystallized from ethyl acetate to provide 0.25 g (44%) of the titled product: IR (KBr, cm-1) 3219, 3048, 1607, 1557, 1236, 1036, 756; 1H NMR (300 MHz, DMSO-d6) δ 11.65 (m, 1H), 10.55 (br s, 1H), 8.1 (m, 1H), 7.75 (m, 1H), 7.3-6.9 (m, 6H), 3.8 (m, 2H), 3.78 (s, 3H), 2.9 (t, J=7 Hz, 2H); MS (FD) m/e 287 (M+) ; UV (EtOH) 290 nm (ε=10141), 267 nm (ε=13121), 247 nm (ε=10959), 202 nm (ε=24078).

Workup

  1. customthe solvent removed in vacuo
  2. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-68d631888e7e4042982527ef7e0c0458
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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