3-Pyridinemethanamine → HCID 24960066, compound

HRID 2381868Notes

Reaction equation

HRID 2381868 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[C:11](=[O:12])[N:10]([C:13]3[S:14][C:15]([C:19](O)=[O:20])=[C:16]([CH3:18])[N:17]=3)[NH:9][C:8]=2[CH3:22])=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.ON1C2C=CC=CC=2N=N1.[NH2:56][CH2:57][C:58]1[CH:59]=[N:60][CH:61]=[CH:62][CH:63]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[C:11](=[O:12])[N:10]([C:13]3[S:14][C:15]([C:19]([NH:56][CH2:57][C:58]4[CH:59]=[N:60][CH:61]=[CH:62][CH:63]=4)=[O:20])=[C:16]([CH3:18])[N:17]=3)[NH:9][C:8]=2[CH3:22])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 310183-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59179705HCID 59179705, compound

Product 1

HCID 24960066HCID 24960066, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-(4-chlorobenzyl)-3-methyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole-5-carboxylic acid (0.05 g, 0.14 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.04 g, 0.20 mmol) and N,N-diisopropylethylamine (0.05 mL, 0.28 mmol) in N,N-dimethylformamide (2 mL) was added 1-hydroxy-benzotriazole (0.05 g, 0.37 mmol). The resulting mixture was stirred at ambient temperature for 15 minutes and 3-(aminomethyl)pyridine (0.02 mL, 0.02 mmol) was added. The reaction mixture was stirred at ambient temperature for 17 hours, diluted with ethyl acetate (30 mL), washed with water and brine. The organic solution was dried over anhydrous sodium sulfate filtered and concentrated in vacuo. The residue was purified by column chromatography to the title compound as a white powder (0.03 g, 48%): mp 215-217° C.: 1H NMR (300 MHz, DMSO-d6) δ 12.31 (br s, 1H), 8.71 (t, J=5.8 Hz, 1H), 8.50 (d, J=1.6 Hz, 1H), 8.42 (dd, J=4.8, 1.6 Hz, 1H), 7.68 (td, J=7.8 Hz, 1.9 Hz, 1H), 7.36-7.19 (m, 5H), 4.38 (d, J=5.8 Hz, 2H), 3.52 (s, 2H), 2.52 (s, 3H), 2.13 (s, 3H); MS (ES+) m/z 454.3 (M+1).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 17 hours
  2. washwashed with water and brine
  3. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography to the title compound as a white powder (0.03 g, 48%)

Sources & evidence

ORD record
ord-a7af598bc1fd4f40a740071eea3f9ce2
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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