Diisopropylethylamine → 4-[2-(5-Bromo-pyridin-2-yloxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester

HRID 14604Notes

Reaction equation

HRID 14604 reaction equation
Cl.[NH2:2][C:3]1[C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][S:6][CH:7]=1.C(N(C(C)C)C(C)C)C.[Br:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][C:30](O)=[O:31])=[N:26][CH:27]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[CH3:11][O:10][C:8]([C:4]1[C:3]([NH:2][C:30](=[O:31])[CH2:29][O:28][C:25]2[CH:24]=[CH:23][C:22]([Br:21])=[CH:27][N:26]=2)=[CH:7][S:6][CH:5]=1)=[O:9]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 3029122-[(5-Bromopyridin-2-yl)oxy]acetic acidHCID 2777609Methyl 4-aminothiophene-3-carboxylate HydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 686917104-[2-(5-Bromo-pyridin-2-yloxy)-acetylamino]-thiophene-3-carboxylic acid methyl esterYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-amino-3-thiophenecarboxylate hydrochloride (500 mg, 2.58 mmol) in dimethylformamide (25 mL) was added N-ethyldiisopropylamine (2.26 mL, 12.9 mmol), (5-bromo-pyridin-2-yloxy)-acetic acid ([79674-66-1], 600 mg, 2.58 mmol) and HATU (1.24 g, 3.23 mmol). The reaction mixture was allowed to stir for 2 hours at room temperature. After such time, water was added, and precipitation was eased by ultrasonication. The precipitate was isolated by filtration and washed with a mixture of water and ethanol (3:1) to yield 4-[2-(5-bromo-pyridin-2-yloxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester (699 mg, 73%) as a light brown solid.

Workup

  1. customprecipitation
  2. customwas eased by ultrasonication
  3. customThe precipitate was isolated by filtration
  4. washwashed with a mixture of water and ethanol (3:1)

Sources & evidence

ORD record
ord-602983a549b047a1bb2106f55a85107c
Source dataset
uspto-grants-2010_06
Patent number
US07732452B2

Reaction notes

Loading…