Hydrochloric Acid → N-(1H-Indol-5-ylmethyl)-2-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetamide

HRID 567861

Reaktionsgleichung

Reaktionsgleichung von HRID 567861
C1C=CC2N(O)N=[N:7]C=2C=1.Cl.CN1CCOCC1.[NH:19]1[C:27]2[C:22](=[CH:23][C:24]([CH2:28][NH2:29])=[CH:25][CH:26]=2)[CH:21]=[CH:20]1.[CH2:30]([N:34]1[CH2:38][CH2:37][CH2:36][C@@H:35]1[CH2:39][NH:40][C:41]1[C:42](=[O:52])[N:43]([CH2:48][C:49](O)=[O:50])[C:44]([CH3:47])=[CH:45][N:46]=1)[CH:31]([CH3:33])[CH3:32]>CN(C)C=O>[NH3:7].[NH:19]1[C:27]2[C:22](=[CH:23][C:24]([CH2:28][NH:29][C:49](=[O:50])[CH2:48][N:43]3[C:44]([CH3:47])=[CH:45][N:46]=[C:41]([NH:40][CH2:39][C@H:35]4[CH2:36][CH2:37][CH2:38][N:34]4[CH2:30][CH:31]([CH3:32])[CH3:33])[C:42]3=[O:52])=[CH:25][CH:26]=2)[CH:21]=[CH:20]1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 54791(1H-indol-5-yl)methanamineHCID 757711-HydroxybenzotriazoleHCID 599005362-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid

Produkt 2

HCID 222AmmoniaHCID 59900500N-(1H-Indol-5-ylmethyl)-2-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetamideAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

HOBT (24 mg, 0.18 mmol), WSCDI.HCl (29 mg, 0.15 mmol), N-methylmorpholine (39 ml, 0.36 mmol) and 1H-indol-5-ylmethylamine (preparation 8) (19 mg, 0.13 mmol) were added to a solution of 2-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid (preparation 62) (38 mg, 0.12 mmol) in N,N-dimethylformamide (2 ml), and the reaction was stirred at room temperature overnight. The mixture was evaporated under reduced pressure and the residue purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (95:5:0.5) as eluant. The product was re-purified using a Biotage™ (KP-Sil™ 60 Å silica gel) cartridge and dichloromethane:methanol:0.88 ammonia (95:5:0.5) as eluant to afford the title compound, (16 mg, 30%).

Aufarbeitung

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue purified by column chromatography on silica gel
  3. customThe product was re-purified

Quellen und Nachweise

ORD-Eintrag
ord-98d86336f98e44278b4f3cb030403ab0
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180627B2

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