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Ammonia → tert-Butyl (3R)-4-[3-(2-{[2-(2-{2-[(tert-butoxycarbonyl)amino]ethoxy}-ethoxy)pyridin-3-yl]oxy}ethoxy)pyrazin-2-yl]-3-methylpiperazine-1-carboxylate

HRID 1765092
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1765092
O1CCCCC1[O:7][CH2:8][CH2:9][O:10][C:11]1[C:12]([O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[N:13][CH:14]=[CH:15][CH:16]=1.N.CC(C)([O-])C.[K+].Cl[C:39]1[C:40]([N:45]2[CH2:50][CH2:49][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:47][C@H:46]2[CH3:58])=[N:41][CH:42]=[CH:43][N:44]=1>CC(O)=O.[Cl-].[Na+].O.O.[Cl-].[Na+].O.C(#N)C>[C:26]([O:25][C:24]([NH:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][C:12]1[C:11]([O:10][CH2:9][CH2:8][O:7][C:39]2[C:40]([N:45]3[CH2:50][CH2:49][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:47][C@H:46]3[CH3:58])=[N:41][CH:42]=[CH:43][N:44]=2)=[CH:16][CH:15]=[CH:14][N:13]=1)=[O:30])([CH3:29])([CH3:28])[CH3:27]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 222AmmoniaHCID 23665647Potassium tert-butoxideHCID 86591089tert-Butyl {2-[2-({3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridin-2-yl}oxy)ethoxy]ethyl}carbamateHCID 86591091(R)-tert-butyl 4-(3-chloropyrazin-2-yl)-3-methylpiperazine-1-carboxylate

Produkt 1

HCID 86591090
tert-Butyl (3R)-4-[3-(2-{[2-(2-{2-[(tert-butoxycarbonyl)amino]ethoxy}-ethoxy)pyridin-3-yl]oxy}ethoxy)pyrazin-2-yl]-3-methylpiperazine-1-carboxylate
Ausbeute 40,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 23713072Sodium chloride dihydrateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

tert-Butyl {2-[2-({3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridin-2-yl}oxy)ethoxy]ethyl}carbamate (from Step 1; 0.74 g, 1.7 mmol) was suspended in 2 M HOAc (5 mL) and acetonitrile (1 mL) and heated at 50° C. for two days. The solution was neutralized with concentrated aqueous ammonia. Brine was added (3 mL) and the mixture was extracted with CHCl3 (×3). The combined organic phases were dried (MgSO4) and the solvent was removed under reduced pressure. The remaining oil was dissolved in dry DMSO (10 mL), potassium tert-butoxide (0.36 g, 3.2 mmol) was added followed by tert-butyl (3R)-4-(3-chloropyrazin-2-yl)-3-methylpiperazine-1-carboxylate (from Example 5; 0.59 g, 1.9 mmol) and the mixture was heated at 50° C. for 20 minutes. The reaction mixture was diluted with water/brine (90:10) and extracted with CHCl3 (×3). The combined organic phases were dried (MgSO4), the solvent was removed under reduced pressure and the remaining oil was chromatographed on a column of silica with hexane/EtOAc (70:30) as eluent to give 0.43 g (40%) of the title compound as a colorless oil. LC-UV purity: system (A) 100%. HRMS m/z calcd for C30H46N6O8 (M)+ 618.3377. found 618.3381. Step 3: {2-[2-({3-[2-({3-[(2R)-2-Methylpiperazin-1-yl]pyrazin-2-yl}oxy)ethoxy]pyridin-2-yl}oxy)ethoxy]ethyl}amine, bis(trifluoroacetate).

Aufarbeitung

  1. extractionthe mixture was extracted with CHCl3 (×3)
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe remaining oil was dissolved in dry DMSO (10 mL)
  5. extractionextracted with CHCl3 (×3)
  6. dry with materialThe combined organic phases were dried (MgSO4)
  7. customthe solvent was removed under reduced pressure
  8. customthe remaining oil was chromatographed on a column of silica with hexane/EtOAc (70:30) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-ac43c76598564435954e6bf2c483f564
Quelldatensatz
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07226925B2

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