Triethylamine → HCID 11150685, compound

HRID 2067169Notes

Reaction equation

HRID 2067169 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]([CH2:5][CH2:6][CH2:7][C:8]#[C:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=O)=[O:4].CCN=C=N[CH2:25][CH2:26][CH2:27][N:28](C)C.C(N(CC)CC)C>ClCCl>[CH:27]1([NH:28][C:13](=[O:15])[C:12]2[CH:16]=[CH:17][CH:18]=[C:10]([C:9]#[C:8][CH2:7][CH2:6][CH2:5][C:3](=[O:4])[N:2]([CH3:1])[CH3:19])[CH:11]=2)[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 114823353-(5-Dimethylcarbamoyl-pent-1-ynyl)-benzoic acid

Product 1

HCID 11150685HCID 11150685, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(5-dimethylcarbamoyl-pent-1-ynyl)-benzoic acid (0.100 g, 0.38 mmol) in dry dichloromethane (1.5 mL) under a nitrogen atmosphere at room temperature, EDCI (0.0728 g, 0.38 mmol) was added followed by triethylamine (0.162 mL, 1.14 mmol), the resulting mixture was stirred at room temperature for further minutes. Cyclopropyilamine (0.027 g, 0.38 mmol) was then added and the mixture stirred at room temperature for 16 hrs. The reaction mixture was washed with a mixture of saturated brine and saturated sodium bicarbonate (1:1; 2×150 mL) followed by saturated brine solution (100 mL). The organic layer was separated and dried over magnesium sulfate and the solvent evaporated under vacuum. The residue was purified by flash column chromatography on silica gel (DCM:MeOH, 95% to 5% methanol gradient) to afford N-cyclopropyl-3-(5-dimethylcarbamoyl-pent-1-ynyl)benzamide (25) (0.10 g, 0.34 mmol, 91% yield).

Workup

  1. additionCyclopropyilamine (0.027 g, 0.38 mmol) was then added
  2. stirringthe mixture stirred at room temperature for 16 hrs
  3. washThe reaction mixture was washed with a mixture of saturated brine and saturated sodium bicarbonate (1:1; 2×150 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent evaporated under vacuum
  7. customThe residue was purified by flash column chromatography on silica gel (DCM:MeOH, 95% to 5% methanol gradient)

Sources & evidence

ORD record
ord-04e33fcdac344c63afa9ccf32a258739
Source dataset
uspto-grants-2012_10
Patent number
US08293796B2

Reaction notes

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