Diisopropylethylamine → HCID 10360449, compound

HRID 1786085Notes

Reaction equation

HRID 1786085 reaction equation
[CH:1]1([N:4]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]([CH3:18])[CH2:9]2)[C:5](=[O:7])[CH3:6])[CH2:3][CH2:2]1.Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:1]1([N:4]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([C:20]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[O:27])[CH:10]([CH3:18])[CH2:9]2)[C:5](=[O:7])[CH3:6])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 21100554HCID 21100554, compound

Product 1

HCID 10360449HCID 10360449, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of N-cyclopropyl-N-(2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-acetamide (82 mg, 0.34 mmol) in DCM (5 mL) was added nicotinoyl chloride hydrochloride (71 mg, 0.40 mmol), followed by DIPEA (104 mg, 0.80 mmol). The reaction mixture was stirred at r.t. for overnight. The mixture was concentrated under reduced pressure and dissolved in ethyl acetate (15 mL). The reaction mixture was washed with sat. sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (hexanes-ethyl acetate system) to afford slightly yellow solid product (81 mg, 68%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutiondissolved in ethyl acetate (15 mL)
  3. washThe reaction mixture was washed with sat. sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by silica gel chromatography (hexanes-ethyl acetate system)

Sources & evidence

ORD record
ord-52d543bd840c486ca4af19ce8488adf5
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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