Hydrochloric Acid → 2-[3-({3-[(2-Aminoethoxy)methyl]phenethyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]-N-[(3-methyl-1H-indol-5-yl)methyl]acetamide

HRID 567849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 567849
Cl.[CH3:2][C:3]1[N:4]([CH2:31][C:32]([NH:34][CH2:35][C:36]2[CH:37]=[C:38]3[C:42](=[CH:43][CH:44]=2)[NH:41][CH:40]=[C:39]3[CH3:45])=[O:33])[C:5](=[O:30])[C:6]([NH:9][CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([CH:27]=[CH:28][CH:29]=2)[CH2:15][O:16][CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C)=[N:7][CH:8]=1.[OH-].[Na+]>CO>[NH3:4].[NH2:19][CH2:18][CH2:17][O:16][CH2:15][C:14]1[CH:13]=[C:12]([CH:29]=[CH:28][CH:27]=1)[CH2:11][CH2:10][NH:9][C:6]1[C:5](=[O:30])[N:4]([CH2:31][C:32]([NH:34][CH2:35][C:36]2[CH:37]=[C:38]3[C:42](=[CH:43][CH:44]=2)[NH:41][CH:40]=[C:39]3[CH3:45])=[O:33])[C:3]([CH3:2])=[CH:8][N:7]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18470880tert-Butyl 2-{[3-(2-{[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}ethyl)benzyl]oxy}ethylcarbamate

Produkt 2

HCID 222AmmoniaHCID 154914892-[3-({3-[(2-Aminoethoxy)methyl]phenethyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]-N-[(3-methyl-1H-indol-5-yl)methyl]acetamideAusbeute 110,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Hydrochloric acid (10 ml, 6N, 60.0 mmol) was added to a solution of tert-butyl 2-{[3-(2-{[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}ethyl)benzyl]oxy}ethylcarbamate (preparation 108) (220 mg, 0.36 mmol) in methanol (10 ml), and the reaction stirred for an hour at room temperature. The mixture was basified using NaOH (1N) solution, and the mixture extracted with ethyl acetate (2×), and dichloromethane (1×). The combined organic extracts were dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (90:10:1) to afford the title compound as a white solid, (100 mg, 55%).

Aufarbeitung

  1. extractionthe mixture extracted with ethyl acetate (2×), and dichloromethane (1×)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7b032c7d867a40dbbd84a759ae7fde39
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180627B2

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