Cyclopropanecarbonyl chloride → HCID 71532775, compound

HRID 1774821Notes

Reaction equation

HRID 1774821 reaction equation
Cl.[CH3:2][N:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:14]=[N:15][CH:16]=[C:17]([O:19][C@H:20]4[CH2:24][CH2:23][NH:22][CH2:21]4)[CH:18]=3)=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:4]1=[O:25].[CH:26]1([C:29](Cl)=[O:30])[CH2:28][CH2:27]1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH:26]1([C:29]([N:22]2[CH2:23][CH2:24][C@H:20]([O:19][C:17]3[CH:18]=[C:13]([C:9]4[CH:8]=[C:7]5[C:12](=[CH:11][CH:10]=4)[N:3]([CH3:2])[C:4](=[O:25])[CH2:5][CH2:6]5)[CH:14]=[N:15][CH:16]=3)[CH2:21]2)=[O:30])[CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 86679170HCID 86679170, compound

Product 1

HCID 71532775HCID 71532775, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-methyl-6-[5-((S)-pyrrolidin-3-yloxy)-pyridin-3-yl]-3,4-dihydro-1H-quinolin-2-one hydrochloride (example 60, 0.05 g, 0.139 mmol) in dry DCM (1.5 mL) was added cyclopropanecarbonyl chloride (0.015 g, 0.139 mmol) followed by TEA (0.035 g, 0.347 mmol) and the reaction mixture was stirred at room temperature for 1 h. Then, the reaction mixture was diluted with EtOAc, poured into sat. NaHCO3 solution (10 mL) and extracted with EtOAc (2×20 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.032 g, 59%) as a colorless foam. MS: 392.2 (M+H+).

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. dry with materialCombined organics were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluting with a 0 to 5% MeOH-DCM gradient

Sources & evidence

ORD record
ord-64d33780db6948a5a347a7021c78a4b6
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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