Cyclopropanecarbonyl chloride → HCID 58579981, compound

HRID 389277Notes

Reaction equation

HRID 389277 reaction equation
Cl.Cl.[CH2:3]([O:5][C:6](=[O:30])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([C:16]2[C:25]([CH2:26][NH:27][CH2:28][CH3:29])=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH:9]=1)[CH3:4].C(N(C(C)C)CC)(C)C.[CH:40]1([C:43](Cl)=[O:44])[CH2:42][CH2:41]1>C(Cl)Cl>[CH2:3]([O:5][C:6](=[O:30])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([C:16]2[C:25]([CH2:26][N:27]([C:43]([CH:40]3[CH2:42][CH2:41]3)=[O:44])[CH2:28][CH3:29])=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 131730234HCID 131730234, compound

Product 1

HCID 58579981HCID 58579981, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[3-(3-Ethylaminomethyl-quinolin-2-yl)-4-methoxy-phenyl]-acetic acid ethyl ester, dihydrochloride (0.40 g, 0.89 mmol) and diisopropylethylamine (1.0 mL, 5.74 mmol) were combined in CH2Cl2 (5 mL) and stirred for 5 minutes. Cyclopropanecarbonyl chloride (0.09 mL, 0.99 mmol) was added, and the reaction was stirred at room temperature until no starting material was seen by analytical LCMS. The mixture was partitioned between CH2Cl2 and saturated aqueous NaHCO3, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (0-75% EtOAc in hexanes) to give the title compound.

Workup

  1. stirringthe reaction was stirred at room temperature until no starting material
  2. customThe mixture was partitioned between CH2Cl2 and saturated aqueous NaHCO3
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel chromatography (0-75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e29371c5a640425aae855787702eb7cd
Source dataset
uspto-grants-2013_02
Patent number
US08378107B2

Reaction notes

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