2-Amino-4-chloropyridine → 5-(2-Aminopyridin-4-ylamino)indole-1-carboxylic acid phenylamide

HRID 2376909

Reaktionsgleichung

Reaktionsgleichung von HRID 2376909
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.Cl.N1C=CC=CC=1.[C:16]1([NH:22][C:23]([N:25]2[C:33]3[C:28](=[CH:29][C:30]([NH2:34])=[CH:31][CH:32]=3)[CH:27]=[CH:26]2)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN1CCCC1=O>[C:16]1([NH:22][C:23]([N:25]2[C:33]3[C:28](=[CH:29][C:30]([NH:34][C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=4)=[CH:31][CH:32]=3)[CH:27]=[CH:26]2)=[O:24])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 5818662-Amino-4-chloropyridineHCID 10176127Pyridinium chlorideHCID 210548515-Aminoindole-1-carboxylic acid phenylamide

Produkt 1

HCID 210548085-(2-Aminopyridin-4-ylamino)indole-1-carboxylic acid phenylamideAusbeute 104 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Amino-4-chloropyridine (500 mg, 0.446 mmol) was dissolved in N-methylpyrrolidone (5.0 ml); pyridine hydrochloride (750 mg) and 5-aminoindole-1-carboxylic acid phenylamide (408 mg, 1.62 mmol) was added thereto; the reaction mixture was stirred at 100° C. for 6.5 hours. After cooling to room temperature, the reaction mixture was partitioned between saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate; the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane-ethyl acetate-methanol system). The obtained pale yellow oil was solidified with diethyl ether; and the crystals were suspended in diethyl ether, filtered off, washed with diethyl ether, and dried to yield the title compound (188 mg, 0.464 mmol, 35.7%) as pale yellow crystals.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane-ethyl acetate-methanol system)
  7. filtrationfiltered off
  8. washwashed with diethyl ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-164d010798e640afb4eb2f42059cf7f2
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468380B2

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