Methyl 3-amino-4-methylthiophene-2-carboxylate → HCID 9884655, compound

HRID 1066254Notes

Reaction equation

HRID 1066254 reaction equation
[C:1]12([CH2:11][C:12](Cl)=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH2:15][C:16]1[C:20]([CH3:21])=[CH:19][S:18][C:17]=1[C:22]([O:24][CH3:25])=[O:23]>N1C=CC=CC=1.ClCCl.C(OCC)(=O)C>[CH3:21][C:20]1[C:16]([NH:15][C:12](=[O:13])[CH2:11][C:1]23[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]4)[CH2:2]2)[CH2:8]3)=[C:17]([C:22]([O:24][CH3:25])=[O:23])[S:18][CH:19]=1

Participants

6

Reactant 2

HCID 123584Methyl 3-amino-4-methylthiophene-2-carboxylateHCID 27718821-Adamantaneacetyl chloride

Product 1

HCID 9884655HCID 9884655, compoundYield 15.1%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-adamantaneacetyl chloride (0.2 g) prepared as described in Example 1a) was added to a solution of methyl 3-amino-4-methylthiophene-2-carboxlate (0.16 g) in pyridine (2 ml) and dichloromethane (4 ml). The reaction mixture was stirred at ambient temperature for 2 days before being diluted with ethyl acetate. The organic phase was then washed with dilute hydrochloric acid and water, dried over magnesium sulphate (MgSO4) and finally concentrated under reduced pressure to give an oil. Purification of the residue by silica gel chromatography, eluitng with 10% ethyl acetate in isohexanes, gave the title compound as a white solid (0.049 g).

Workup

  1. washThe organic phase was then washed with dilute hydrochloric acid and water
  2. dry with materialdried over magnesium sulphate (MgSO4)
  3. concentrationfinally concentrated under reduced pressure
  4. customto give an oil
  5. customPurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-19a9880dab19499aa867a275a8c570f5
Source dataset
uspto-grants-2001_06
Patent number
US06242470B1

Reaction notes

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