5-Chloro-1H-indole-2-carboxylic acid → HCID 59676891, compound

HRID 902858Notes

Reaction equation

HRID 902858 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.[OH2:14].O[N:16]1[C:20]2[CH:21]=CC=[CH:24][C:19]=2[N:18]=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[NH2:18][C@@H:19]1[CH2:24][O:14][CH2:21][C@@H:20]1[NH:16][C:11]([C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)=[O:13]

Participants

5

Reactant 3

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 59676891HCID 59676891, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

5-Chloroindole-2-carboxylic acid (0.29 g), 1-hydroxybenzotriazole monohydrate (0.2 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.6 g) were successively added to a solution of the compound (0.5 g) obtained in Referential Example 171 in N,N-dimethylformamide (10 ml), and the mixture was heated and stirred at 50° C. for a day. The reaction mixture was concentrated, and the resultant residue was diluted with a mixed solvent composed of chloroform and methanol (9:1) and washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride. After the resultant organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the resultant residue was purified by column chromatography on silica gel (chloroform:methanol=95:5) to obtain the title compound (0.2 g).

Workup

  1. temperaturethe mixture was heated
  2. concentrationThe reaction mixture was concentrated
  3. additionthe resultant residue was diluted with a mixed solvent
  4. washwashed with a saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride
  5. dry with materialAfter the resultant organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe resultant residue was purified by column chromatography on silica gel (chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-1462fc28bbc248808a842e297e803477
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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