1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 2381815Notes

Reaction equation

HRID 2381815 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[S:14][C:15]([C:19]([OH:21])=O)=[C:16]([CH3:18])[N:17]=2)[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.[N:52]1[CH:57]=[CH:56][CH:55]=[C:54]([CH2:58][NH2:59])[CH:53]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[S:14][C:15]([C:19]([NH:59][CH2:58][C:54]3[CH:53]=[N:52][CH:57]=[CH:56][CH:55]=3)=[O:21])=[C:16]([CH3:18])[N:17]=2)[N:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 310183-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 591796642-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 249574722-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 61.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acid (0.20 g, 0.67 mmol) in anhydrous N,N-dimethylformamide (3 mL) was added 1-hydroxybenzotriazole (0.23 g, 1.73 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.17 g, 0.87 mmol), N,N-diisopropylethylamine (0.15 mL, 0.87 mmol) and pyridin-3-ylmethanamine (0.081 mL, 0.80 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with ethyl acetate (15 mL) and washed with saturated aqueous sodium bicarbonate (5 mL) and brine (5 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The obtained solid was washed with 5% ethyl acetate in hexanes and dried in air to afford the title compound as a white solid (0.16 g, 60%): mp 212-213° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.53 (br s, 1H), 7.98-7.95 (m, 1H), 7.73-7.66 (m, 1H), 7.43-7.22 (m, 6H), 6.28 (t, J=5.6 Hz, 1H), 5.55 (s, 2H), 4.61 (d, J=5.6 Hz, 2H), 2.67 (s, 3H); MS (ES+) m/z 391.3 (M+1).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (5 mL) and brine (5 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe obtained solid was washed with 5% ethyl acetate in hexanes
  6. customdried in air

Sources & evidence

ORD record
ord-6761d99a9bd6409c8c8c62de886db2ac
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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