Dimethylamine → HCID 71186206, compound

HRID 1470511Notes

Reaction equation

HRID 1470511 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12](O)=[O:13])=[CH:9][CH:8]=[C:7]2[O:15][CH3:16].O=S(Cl)Cl.C[CH2:22][N:23](C(C)C)[CH:24](C)C.CNC>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]([N:23]([CH3:24])[CH3:22])=[O:13])=[CH:9][CH:8]=[C:7]2[O:15][CH3:16]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 71185803HCID 71185803, compound

Product 1

HCID 71186206HCID 71186206, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 8-chloro-4-methoxy-1-naphthoic acid (step-4 intermediate) (0.5 g, 2.11 mmol) in CH2Cl2 (5 mL) was added, SOCl2 (0.31 mL, 4.22 mmol, 2.0 eq.) and the mixture was stirred at RT for 3 h. The solvent was evaporated under reduced pressure and the crude product was dissolved in DCM (10 mL). To this, DIPEA (0.74 mL, 4.23 mmol) was added followed by dimethylamine (1.5 eq.) and the reaction mixture was stirred at RT for 3 h and then quenched with ice. The aqueous layer was extracted with dichloromethane and the combined organic layer was washed with sat. NaHCO3 solution, water, brine, dried over Na2SO4 and filtered. The solvent was evaporated to provide the desired amide derivative (528 mg, 95%) this was used in the next step without any further purification.

Workup

  1. additionwas added
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe crude product was dissolved in DCM (10 mL)
  4. customquenched with ice
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. washthe combined organic layer was washed with sat. NaHCO3 solution, water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5e4f5121cba14064a662525ce0cfd321
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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