Indole-2-carboxylic acid → HCID 86616537, compound

HRID 884155Notes

Reaction equation

HRID 884155 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:22]=[CH:21][C:12]([CH2:13][CH:14]3[S:18][C:17](=[O:19])[NH:16][C:15]3=[O:20])=[CH:11][C:10]=2[CH3:23])=[N:6][CH:7]=1.[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]1[C:33](O)=[O:34].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[O:19]=[C:17]1[NH:16][C:15](=[O:20])[CH:14]([CH2:13][C:12]2[CH:21]=[CH:22][C:9]([O:8][C:5]3[N:6]=[CH:7][C:2]([NH:1][C:33]([C:25]4[NH:24][C:32]5[C:27]([CH:26]=4)=[CH:28][CH:29]=[CH:30][CH:31]=5)=[O:34])=[CH:3][CH:4]=3)=[C:10]([CH3:23])[CH:11]=2)[S:18]1

Participants

6

Reactant 4

HCID 72899Indole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86616538HCID 86616538, compound

Product 1

HCID 86616537HCID 86616537, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[4-(5-aminopyridin-2-yloxy)-3-methylbenzyl]thiazolidine-2,4-dione (150 mg, 0.46 mmol) in DMF (5 mL) were added indole-2-carboxylic acid (74 mg, 0.46 mmol), 1-hydroxybenzotriazole monohydrate (70 mg, 0.46 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (110 mg, 0.57 mmol), and the resulting solution was stirred for 5 days at room temperature. This reaction solution was concentrated under reduced pressure. Water was added to the residue, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, evaporated, and the residue was then purified by silica gel column chromatography (chloroform:methanol=30:1). To the obtained powdery substance was added ethanol, the resulting solution was filtered and the filtrate was washed with ethanol, to thereby yield 100 mg of the title compound.

Workup

  1. concentrationThis reaction solution was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customthe residue was then purified by silica gel column chromatography (chloroform:methanol=30:1)
  8. additionTo the obtained powdery substance was added ethanol
  9. filtrationthe resulting solution was filtered
  10. washthe filtrate was washed with ethanol

Sources & evidence

ORD record
ord-0cabac6eefbf496cb1eca9c252113e6f
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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