Oxalyl chloride → N-Cyclopropyl-3-[3-(methyloxy)propyl]-1-naphthalenecarboxamide

HRID 337565Notes

Reaction equation

HRID 337565 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([C:16]([OH:18])=O)[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.C(Cl)(=O)C(Cl)=O.CC[N:27]([CH:31]([CH3:33])[CH3:32])C(C)C.C1(N)CC1>CN(C=O)C.C(Cl)Cl>[CH:31]1([NH:27][C:16]([C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:15]=[C:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=2)=[O:18])[CH2:33][CH2:32]1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 668963483-[3-(Methyloxy)propyl]-1-naphthalenecarboxylic acid

Product 1

HCID 66896522N-Cyclopropyl-3-[3-(methyloxy)propyl]-1-naphthalenecarboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 solution (0.1 M) of 3-[3-(methyloxy)propyl]-1-naphthalenecarboxylic acid (1 eq.) from the previous step was added at 0° C. oxalyl chloride (1.2 eq.) followed by a few drops of DMF. The resulting solution was stirred at RT for 2 h before the volatiles were removed in vacuo. The resulting residue was taken up in dichloromethane (0.1 M), cooled to 0° C. and added sequentially Hunig's base (1.2 eq.) an cyclopropylamine (1.1 eq.) dropwise. The resulting suspension was stirred at RT for 18 h. The reaction was quenched with 1 N aq. HCl and extracted with ether. The combined organic extracts were washed further with 1 N aq. NaOH, water and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a white solid.

Workup

  1. customwere removed in vacuo
  2. temperaturecooled to 0° C.
  3. stirringThe resulting suspension was stirred at RT for 18 h
  4. customThe reaction was quenched with 1 N aq. HCl
  5. extractionextracted with ether
  6. washThe combined organic extracts were washed further with 1 N aq. NaOH, water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-88287556e31f4dceb63f2c5a09a9f86c
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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