Pyridine → N-Benzyl-4-methyl-2-(5-phenylpentanamido)thiazole-5-carboxamide

HRID 45379Notes

Reaction equation

HRID 45379 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:24]1([CH2:30][CH2:31][CH2:32][CH2:33][C:34](Cl)=[O:35])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1.ClCCl.CN(C1C=CC=CN=1)C>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acidHCID 109654605-phenylpentanoyl Chloride

Product 1

HCID 59369684N-Benzyl-4-methyl-2-(5-phenylpentanamido)thiazole-5-carboxamideYield 98.2%

Reagents, catalysts & solvents 3

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled mixture of 2-amino-4-methylthiazole-5-carboxylic acid benzylamide (0.10 g, 0.40 mmol), pyridine (0.096 g, 1.21 mmol), and dimethylaminopyridine (0.010 mg) in anhydrous tetrahydrofuran (5 mL) was added 5-phenylpentanoyl chloride (0.16 g, 0.81 mmol) in anhydrous dichloromethane (1 mL) dropwise. The reaction mixture was stirred at ambient temperature for 2 hours, then diluted with dichloromethane (10 mL) and washed with saturated sodium bicarbonate solution (2×5 mL), 1 N hydrochloric acid (5 mL), and brine (5 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrate in vacuo. The residue was purified by column chromatography over silica gel, eluting with ethyl acetate/hexanes (1/1) to afford the title compound as a clear oil (0.16 g, 97%) %); 1H NMR (CDCl3, 300 MHz) δ 11.19 (s, br, 1H), 7.33-7.09 (m, 10H), 6.40 (t, J=4.8 Hz, 1H), 4.58 (d, J=5.8 Hz, 2H), 2.60-2.39 (m, 7H), 1.74-1.56 (m, 4H); MS (ES+) m/z 408.6 (M+1).

Workup

  1. washwashed with saturated sodium bicarbonate solution (2×5 mL), 1 N hydrochloric acid (5 mL), and brine (5 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrate in vacuo
  5. customThe residue was purified by column chromatography over silica gel
  6. washeluting with ethyl acetate/hexanes (1/1)

Sources & evidence

ORD record
ord-d47a195e5c63486b8f9d6aa68013c626
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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