Triethylamine → HCID 68491830, compound

HRID 2381847Notes

Reaction equation

HRID 2381847 reaction equation
[N:1]([C:4]1[S:5][C:6]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[C:7]([CH3:9])[N:8]=1)=[N+:2]=[N-:3].[C:20]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:21][C:22]([CH3:24])=O.C(N(CC)CC)C>CN(C)C=O.ClCCl>[CH2:13]([NH:12][C:10]([C:6]1[S:5][C:4]([N:1]2[C:22]([CH3:24])=[C:21]([C:20]([O:26][CH2:27][CH3:28])=[O:25])[N:3]=[N:2]2)=[N:8][C:7]=1[CH3:9])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8868Ethyl AcetoacetateHCID 73213267HCID 73213267, compound

Product 1

HCID 68491830HCID 68491830, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-azido-N-benzyl-4-methylthiazole-5-carboxamide (0.53 g, 1.92 mmol) and ethyl acetoacetate (0.50 g, 3.85 mmol) in N,N-dimethylformamide (2 mL) was added triethylamine (0.54 mL, 3.85 mmol). The reaction mixture was stirred at ambient temperature for 24 hours, diluted with dichloromethane (30 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 the filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a white solid in 49% yield (0.36 g): 1H NMR (300 MHz, DMSO-d6) δ 9.03 (t, J=6.0 Hz, 1H), 7.36-7.34 (m, 5H), 4.46 (d, J=6.0 Hz, 2H), 4.35 (q, J=6.0 Hz, 2H), 2.89 (s, 3H), 2.64 (s, 3H), 1.34 (t, J=6.0 Hz, 3H); MS (ES+) m/z 386.3 (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. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6b10591f61e14305bb2c081c3fdd8321
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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