4-Fluorobenzylamine → HCID 59481183, compound

HRID 560864Notes

Reaction equation

HRID 560864 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[C:12](=[O:13])[N:11]([C:14]2[S:15][C:16]([C:20](=[O:29])[NH:21][CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[C:17]([CH3:19])[N:18]=2)[CH:10]=[N:9]1)(=O)=O.[F:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][NH2:38])=[CH:33][CH:32]=1>CO>[F:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][NH:38][CH2:6][CH2:7][N:8]2[C:12](=[O:13])[N:11]([C:14]3[S:15][C:16]([C:20]([NH:21][CH2:22][C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)=[O:29])=[C:17]([CH3:19])[N:18]=3)[CH:10]=[N:9]2)=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 594812642-(4-(4-methyl-5-(pyridin-3-ylmethylcarbamoyl)thiazol-2-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)ethyl methanesulfonate

Product 1

HCID 59481183HCID 59481183, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(4-(4-methyl-5-(pyridin-3-ylmethylcarbamoyl)thiazol-2-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)ethyl methanesulfonate (0.10 g, 0.23 mmol) and (4-fluorophenyl)methanamine (0.09 g, 0.69 mmol) in anhydrous methanol (5 mL) was heated at reflux for 6 hours. The solvent was removed in vacuo and the residue was purified by column chromatography eluted with ethyl acetate to afford the title compound as a white solid in 66% yield (0.07 g): mp 106-107° C. (ethyl acetate/hexane); 1H NMR (300 MHz, CDCl3) δ 8.59 (br s, 1H), 8.56-8.47 (m, 1H), 8.25 (s, 1H), 7.73-7.65 (m, 1H), 7.32-7.18 (m, 3H), 7.00-6.89 (m, 2H), 6.44 (t, J=5.8 Hz, 1H), 4.59 (d, J=5.8 Hz, 2H), 3.98 (t, J=5.8 Hz, 2H), 3.77 (s, 2H), 3.00 (t, J=5.8 Hz, 2H), 2.64 (s, 3H): MS (ES+) m/z 468.2 (M+1).

Workup

  1. temperatureat reflux for 6 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography
  4. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-60189591553842399b940a8d604378c2
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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