Cyclopropanecarbonyl chloride → HCID 71231639, compound

HRID 2175372Notes

Reaction equation

HRID 2175372 reaction equation
C(N(C(C)C)CC)(C)C.[CH:10]1([C:13](Cl)=[O:14])[CH2:12][CH2:11]1.Cl.[N:17]1([C:24]([C:26]2[CH:27]=[C:28]3[NH:37][C:36](=[O:38])[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]3[CH:39]=2)=[O:25])[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>CN(C)C=O.C(OCC)(=O)C>[CH:10]1([C:13]([N:20]2[CH2:21][CH2:22][CH2:23][N:17]([C:24]([C:26]3[CH:27]=[C:28]4[NH:37][C:36](=[O:38])[C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:29]4[CH:39]=3)=[O:25])[CH2:18][CH2:19]2)=[O:14])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 86731174HCID 86731174, compound2×

Product 1

HCID 71231639HCID 71231639, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diisopropylethylamine (0.11 mL, 0.63 mmol) and cyclopropane carbonyl chloride (30 μL, 0.33 mmol) were sequentially added to a solution of 2-(homopiperazine-1-carbonyl)pyrrolo[1,2-a]quinazolin-5(4H)-one hydrochloride (Compound 5-1, 70.0 mg, 0.20 mmol) in anhydrous N,N-dimethylformamide (0.50 mL), and the reaction solution was stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate (20 mL), and washed sequentially with 0.1M sodium hydroxide aqueous solution (20 mL) and brine (20 mL). The aqueous layer was extracted twice with chloroform (20 mL), and combined with the ethyl acetate layer, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the obtained residue was purified by silica gel column chromatography (ethyl acetate), to obtain the title compound (25.8 mg, yield: 34%) as a colorless powder.

Workup

  1. washwashed sequentially with 0.1M sodium hydroxide aqueous solution (20 mL) and brine (20 mL)
  2. extractionThe aqueous layer was extracted twice with chloroform (20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-4bf27a4e0384468bab29bbce07dd19fa
Source dataset
uspto-grants-2015_06
Patent number
US09062061B2

Reaction notes

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