Dimethylacetamide → HCID 57901871, compound

HRID 1851566Notes

Reaction equation

HRID 1851566 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[NH:8][C:7]=12.[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[S:20](Cl)(=[O:22])=[O:21].CN(C)C(=O)C>C(OCC)(=O)C>[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[S:20]([NH:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[NH:8][C:7]=12)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 855182-Thiophenesulfonyl chlorideHCID 57901694HCID 57901694, compound

Product 1

HCID 57901871HCID 57901871, compoundYield 1.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of methyl 7-amino-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (0.40 g), thiophene-2-sulfonyl chloride (0.48 g) and N,N-dimethylacetamide (20 ml) was stirred at 120° C. for 18 hr. The reaction solution was diluted with ethyl acetate, washed with aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=2:8-1:1) to give the title compound (10.5 mg, yield 1.5%) as pale-yellow crystals. melting point 159-160° C.

Workup

  1. washwashed with aqueous sodium hydrogencarbonate solution, water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ba18e3baaaf447d7b52ee3730d50b954
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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