Dimethylformamide → HCID 67394627, compound

HRID 1023718Notes

Reaction equation

HRID 1023718 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([OH:14])=O)[S:7][C:8]=1[CH:9]([CH3:11])[CH3:10])([CH3:3])[CH3:2].S(Cl)(Cl)=O.C[N:20](C)C=O.N[C:25]1[C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=[CH:27][N:26]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([NH:20][C:27]2[N:26]=[CH:25][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=2)=[O:14])[S:7][C:8]=1[CH:9]([CH3:10])[CH3:11])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 351633Methyl 2-aminopyridine-3-carboxylateHCID 58420519HCID 58420519, compound

Product 1

HCID 67394627HCID 67394627, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

In the same manner as that of Example 9, 4,5-diisopropylthiophene-2-carboxylic acid (180 mg, 0.849 mmol) was converted to an acid chloride with thionyl chloride and dimethylformamide. This acid chloride was dissolved in pyridine (4 ml), the solution was added with methyl 2-aminopyridine-3-carboxylate (258 mg, 1.70 mmol) and 4-dimethylaminopyridine (5 mg, 41 μmol), and the mixture was stirred at room temperature for 48 hours. The reaction mixture was treated in a conventional manner, and then the resultant was purified by silica gel chromatography [benzene-ethyl acetate (4:1)] to obtain methyl 6-[(4,5-diisopropylthiophene-2-carbonyl)amino]pyridine-3-carboxylate (98 mg, 33%) as colorless foam, together with the collected starting material (67 mg, 37%).

Workup

  1. additionThe reaction mixture was treated in a conventional manner
  2. customthe resultant was purified by silica gel chromatography [benzene-ethyl acetate (4:1)]

Sources & evidence

ORD record
ord-0a63f75389e1423a9cabede3a12ddcc5
Source dataset
uspto-grants-2014_05
Patent number
US08722730B2

Reaction notes

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