Cyclopropanecarbonyl chloride → HCID 52175163, compound

HRID 1865870Notes

Reaction equation

HRID 1865870 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].CCN(C(C)C)C(C)C.[CH:20]1([C:23](Cl)=[O:24])[CH2:22][CH2:21]1>ClCCl>[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH:7][C:23]([CH:20]1[CH2:22][CH2:21]1)=[O:24]

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 27249803-Bromobenzylamine hydrochloride

Product 1

HCID 52175163HCID 52175163, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromo-benzylamine hydrochloride (437.3 mg, 2.0 mmol) was dissolved in dichloromethane (15 mL), and the solution was cooled to 0° C. DIEA (688.0 μL, 3.9 mmol) was then added, and the reaction was stirred at 0° C. for 5 minutes. Then cyclopropanecarbonyl chloride (180.0 μL, 2.3 mmol) was added, and the reaction was stirred at 0° C. for 20 minutes. The reaction was quenched with distilled water, and the solvents were removed. The resulting mixture was redissolved in DMF (10 mL) and purified by reverse phase HPLC to give the desired product.

Workup

  1. stirringthe reaction was stirred at 0° C. for 20 minutes
  2. customThe reaction was quenched with distilled water
  3. customthe solvents were removed
  4. dissolutionThe resulting mixture was redissolved in DMF (10 mL)
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-2516867814594b4d8b55a4b030311c34
Source dataset
uspto-grants-2009_12
Patent number
US07629340B2

Reaction notes

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