Benzylamine → HCID 24984927, compound

HRID 1887258Notes

Reaction equation

HRID 1887258 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:12][C:11]2=[O:22])[S:5][C:6]=1[C:7](O)=[O:8].ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.[CH2:53]([NH2:60])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>CN(C)C=O>[CH2:53]([NH:60][C:7]([C:6]1[S:5][C:4]([N:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][C:11]2=[O:22])=[N:3][C:2]=1[CH3:1])=[O:8])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

7

Reactant 5

HCID 7504BenzylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 24985951HCID 24985951, compound

Product 1

HCID 24984927HCID 24984927, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methyl-2-(2-oxo-4-phenylpyridin-1(2H)-yl)thiazole-5-carboxylic acid (0.20 g, 0.64 mmol) in anhydrous N,N-dimethylformamide (3 mL) was added 1-hydroxybenzotriazole (0.23 g, 1.67 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.15 g, 0.77 mmol), N,N-diisopropylethylamine (0.11 g, 0.83 mmol), and benzylamine (0.084 mL, 0.77 mmol). The reaction mixture was stirred at ambient temperature for 5 hours and N,N-dimethylformamide was removed in vacuo. The residue was dissolved in ethyl acetate (15 mL) and washed with saturated aqueous sodium bicarbonate (2×5 mL) and brine (5 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a white solid (0.12 g, 47%): mp 235-237° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 8.83 (t, J=5.8 Hz, 1H), 8.77 (d, J=7.6 Hz, 1H), 7.87-7.77 (m, 2H), 7.52-7.49 (m, 3H), 7.34-7.18 (m, 5H), 7.08-7.00 (m, 2H), 4.40 (d, J=5.8 Hz, 2H), 2.59 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.9, 160.4, 153.7, 151.4, 150.6, 139.9, 135.9, 131.6, 130.9, 129.7, 128.8, 127.8, 127.5, 127.3, 124.5, 43.2, 17.6; MS (ES+) m/z 402.5 (M+1).

Workup

  1. customN,N-dimethylformamide was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (15 mL)
  3. washwashed with saturated aqueous sodium bicarbonate (2×5 mL) and brine (5 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-198de7af433045f1a087472fef652639
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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