Potassium Carbonate → 6-[2-(Cyclopropanecarbonyl-amino)-pyridin-4-yloxy]-isoquinoline-1-carboxylic acid

HRID 1512191Notes

Reaction equation

HRID 1512191 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]([CH:13]2[CH2:15][CH2:14]2)=[O:12])[CH:5]=1)([O-])=O.[OH:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23]([C:27]([OH:29])=[O:28])=[N:22][CH:21]=[CH:20]2.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH:13]1([C:11]([NH:10][C:6]2[CH:5]=[C:4]([O:16][C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[C:23]([C:27]([OH:29])=[O:28])=[N:22][CH:21]=[CH:20]4)[CH:9]=[CH:8][N:7]=2)=[O:12])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 58902368N-(4-nitropyridin-2-yl)cyclopropanecarboxamideHCID 136304046HCID 136304046, compound

Product 1

HCID 685888926-[2-(Cyclopropanecarbonyl-amino)-pyridin-4-yloxy]-isoquinoline-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
20 °C

Procedure

Cyclopropanecarboxylic acid (4-nitro-pyridin-2-yl)-amide (200 mg, 0.965 mmol), 6-hydroxy-isoquinoline-1-carboxylic acid (183 mg, 0.965 mmol), and potassium carbonate (267 mg, 1.93 mmol) are stirred in dimethylsulphoxide (10 mL) at 90° C. for 24 h. After cooling to 20° C., the dimethylsulphoxide is partially evaporated under reduced pressure, water is added, the solution is carefully acidified with trifluoroacetic acid and the resulting solution is purified using a MPLC reverse phase chromatography (Merck LiChroprep® RP-18, acetonitrile/water 0.1% trifluoroacetic acid) to afford the title compound as a solid. M-H, 348.1; HPLC tR: 3.29 min.

Workup

  1. customthe dimethylsulphoxide is partially evaporated under reduced pressure, water
  2. additionis added
  3. customthe resulting solution is purified

Sources & evidence

ORD record
ord-e4c033431978479f8cf52ca5936e96d5
Source dataset
uspto-grants-2012_07
Patent number
US08217045B2

Reaction notes

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