Triethylamine → HCID 58842336, compound

HRID 1270442Notes

Reaction equation

HRID 1270442 reaction equation
[CH3:1][O:2][C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[C:12](Cl)(=O)[C:13](Cl)=O.[CH2:18](N(CC)CC)[CH3:19].[CH2:25]1[C@@H:27]([NH2:28])[C@@H:26]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl.CN(C)C=O>[CH3:1][O:2][C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([NH:28][CH2:27][C:26]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:25][CH2:13][CH2:12][CH2:19][CH2:18]1)=[O:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 19493(1R,2S)-TranylcypromineHCID 65578Oxalyl chlorideHCID 7080932-Methoxynicotinic acid

Product 1

HCID 58842336HCID 58842336, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 2-methoxynicotinic acid (0.23 g; 1.5 mmol) in methylene chloride (15 ml) was treated with oxalyl chloride (0.14 mL; 1.6 mmol) and 2 drops of N,N-dimethylformamide. The reaction mixture was allowed to stir at room temperature for 30 minutes at which time triethylamine (0.3 mL; 2.2 mmol) and compound 1 (0.315 g; 1.66 mmol). After an additional 15 minutes of stirring the reaction mixture was washed with water and saturated aqueous sodium chloride, dried (magnesium sulfate) and concentrated. The crude residue was purified by column chromatography on silicia gel using 7:3 hexane:ethyl acetate as the eluent to give 0.37 g of 2-Methoxy-N-(1-phenyl-cyclohexylmethyl)-nicotinamide as a white solid. Mass Spec [M+H]+=325.

Workup

  1. washwas washed with water and saturated aqueous sodium chloride
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated
  4. customThe crude residue was purified by column chromatography on silicia gel

Sources & evidence

ORD record
ord-8f3d62aee1174481b98f945638bf99b1
Source dataset
uspto-grants-2007_04
Patent number
US07202253B2

Reaction notes

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