Triethylamine → HCID 22340371, compound

HRID 585314Notes

Reaction equation

HRID 585314 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21]O)[CH:17]=3)[CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[CH2:23]([N:25](CC)[CH2:26]C)C.CS(Cl)(=O)=O.Cl.CNC.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:25]([CH3:26])[CH3:23])[CH:17]=3)[CH:12]=2)=[O:10])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 22340417HCID 22340417, compound

Product 1

HCID 22340371HCID 22340371, compoundYield 35.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The N-(4-bromophenyl)-6-(hydroxymethyl)-2-naphthamide (349 mg, 0.980 mmol) obtained in Reference Example 4 and triethylamine (0.164 ml, 1.18 mmol) were dissolved in N,N-dimethylformamide (5 ml), methanesulfonyl chloride (0.091 ml, 18 mmol) was added thereto under ice-cooling, and the mixture was stirred for 30 minutes. To the reaction solution were added dimethylamine hydrochloride (160 mg, 96 mmol) and potassium carbonate (406 mg, 2.94 mmol), and the mixture was stirred at 60° C. for 16 hours. To the reaction solution were added ethyl acetate and water, and the mixture was extracted with ethyl acetate. The extract was washed with an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the residue was added diisopropyl ether, followed by crystallization to obtain the titled compound (135 mg) as a white powder.

Workup

  1. temperatureunder ice-cooling
  2. stirringthe mixture was stirred at 60° C. for 16 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue was added diisopropyl ether
  8. customfollowed by crystallization

Sources & evidence

ORD record
ord-18ce2ce7ff85472ea42dc7d9206ab901
Source dataset
uspto-grants-2005_08
Patent number
US06930185B2

Reaction notes

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