3-Pyridinemethanamine → HCID 25095926, compound

HRID 560879Notes

Reaction equation

HRID 560879 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]2=[O:21])[S:4][C:3]=1[C:22](O)=[O:23].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)C(C)C)(C)C.[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>[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][O:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:8]2=[O:21])[S:4][C:3]=1[C:22]([NH:56][CH2:57][C:58]1[CH:59]=[N:60][CH:61]=[CH:62][CH:63]=1)=[O:23]

Participants

8

Reactant 5

HCID 310183-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 580314563-Methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acid

Product 1

HCID 25095926HCID 25095926, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 3-methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acid (0.08 g, 0.23 mmol), 1-hydroxybenzotriazole (0.05 g, 0.35 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.07 g, 0.35 mmol) in N,N-dimethylformamide (2 mL) was added N,N-diisopropylethylamine (0.12 mL, 0.70 mmol), followed by the addition of 3-(aminomethyl)pyridine (0.02 mL, 0.24 mmol). The resulting reaction mixture was stirred at ambient temperature for 18 h, and then diluted with ethyl acetate (75 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (3×35 mL) and water (35 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with ethyl acetate in hexanes to afford the title compound as a colorless solid in 79% yield (0.08 g): mp 78-80° C.; 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.52 (s, 1H), 7.69 (d, J=7.8 Hz, 1H), 7.32-7.23 (m, 3H), 6.96 (t, J=7.6 Hz, 1H), 6.88 (d, J=7.6 Hz, 2H), 6.15 (t, J=5.7 Hz, 1H), 6.08 (s, 1H), 4.57 (d, J=5.7 Hz, 2H), 4.15 (t, J=4.9 Hz, 2H), 3.80 (br s, 4H), 3.69 (t, J=4.9 Hz, 2H), 2.48 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 163.5, 158.2, 156.0, 149.2, 148.8, 142.5, 141.7, 135.5, 129.6, 123.6, 121.2, 118.9, 114.3, 112.4, 66.9, 43.8, 43.0, 41.2, 16.1; MS (ES+) m/z 437.4 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (3×35 mL) and water (35 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1f55c53133a145248e23b3e7d0bb3d3d
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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