Acetone → 6-Acetyl-2-amino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080198Notes

Reaction equation

HRID 2080198 reaction equation
[NH2:1][C:2]1[N:23]=[C:22]([C:24]([O:26]CC)=[CH2:25])[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].CC(C)=O.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O>[C:24]([C:22]1[CH:21]=[CH:20][C:3]([C:4]([NH:6][CH2:7][C:8]2[S:9][C:10]([O:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:11][CH:12]=2)=[O:5])=[C:2]([NH2:1])[N:23]=1)(=[O:26])[CH3:25]

Participants

7

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 231303892-Amino-6-(1-ethoxyvinyl)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

Product 1

HCID 231304466-Acetyl-2-amino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamideYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-amino-6 (1-ethoxy vinyl)-N-(5-phenoxy-thiophene-2-ylmethyl)-nicotinamide described in Preparation Example A+-14 (2.0 mg, 0.0051 mmol) and acetone (2 mL) were added water (1 mL) and concentrated sulfuric acid (0.2 mL), and the solution was stirred at room temperature for 3 hours. The reaction solution was neutralized with an aqueous solution of saturated sodium bicarbonate, and ethyl acetate was added for extraction. The organic layer was washed with brine, the solvent was then evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1), and the title compound (1.0 mg, 0.0027 mmol, 53%) was obtained as a white solid.

Workup

  1. additionwas added for extraction
  2. washThe organic layer was washed with brine
  3. customthe solvent was then evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-90b674e9cd6341f290d3d861cf6a5021
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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