HCID 11994313, Verbindung → N-{5-[Methoxy(phenyl)acetyl]-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-yl}-4-(4-methylpiperazin-1-yl)benzene-1-carboximidic acid

HRID 729242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 729242
[CH3:1][O:2][C@H:3]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:4]([N:6]1[CH2:13][C:12]2[C:11]([NH:14][C:15](=[O:29])[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[N:10][N:9](C(OCC)=O)[C:8]=2[CH2:7]1)=[O:5]>CO.C(N(CC)CC)C>[CH3:1][O:2][C@H:3]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:4]([N:6]1[CH2:13][C:12]2[C:11]([NH:14][C:15](=[O:29])[C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)=[CH:20][CH:21]=3)=[N:10][NH:9][C:8]=2[CH2:7]1)=[O:5]

Komponenten

4

Edukt 1

HCID 11994313HCID 11994313, Verbindung

Produkt 1

HCID 11442891N-{5-[Methoxy(phenyl)acetyl]-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-yl}-4-(4-methylpiperazin-1-yl)benzene-1-carboximidic acidAusbeute 46,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution of ethyl 5-[(2R)-2-methoxy-2-phenylethanoyl]-3-{[4-(4-methylpiperazin-1-yl)benzoyl]amino}-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate (3.94 g, 7.2 mmol) in methanol (MeOH, 130 ml) and triethylamine (Et3N, 13 ml) was stirred at room temperature for 16 hours (some precipitation occurred). The solid was separated and washed with Et2O, to give 1.6 g of the title compound. Solution was evaporated up to few milliliters, and a second fraction of solid product was separated (1.62 g). The two fractions were joined and analyzed by LC-MS (purity around 90% 254 and 220 nM). After chromatographic purification (short silica gel column, DCM/MeOH 45:5) 2.83 g (83%) of the title compound were obtained as a white solid. M.p 289° C.; [M+H]+ 475;

Aufarbeitung

  1. customsome precipitation
  2. customThe solid was separated
  3. washwashed with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-1b031b364ce04fb6be8dadce67a60bba
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582628B2

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