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Dichloromethane → HCID 178423523, Verbindung

HRID 454332
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 454332
FC(F)(F)C(O)=O.[CH3:8][C:9]1[CH:14]=[C:13]([C:15]2[N:19](C3CCCCO3)[CH:18]=[N:17][N:16]=2)[CH:12]=[CH:11][C:10]=1[C:26]1[N:31]=[C:30]2[NH:32][C:33]3([CH2:38][CH2:37]3)[C:34](=[O:36])[NH:35][C:29]2=[N:28][CH:27]=1.CC1C=C(C2N(C3CCCCO3)C=NN=2)C=CC=1B1OC(C)(C)C(C)(C)O1.BrC1N=C2NC3(CC3)C(=O)NC2=NC=1.ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(O)(C)C.O1CCOCC1>[CH3:8][C:9]1[CH:14]=[C:13]([C:15]2[NH:19][CH:18]=[N:17][N:16]=2)[CH:12]=[CH:11][C:10]=1[C:26]1[N:31]=[C:30]2[NH:32][C:33]3([CH2:37][CH2:38]3)[C:34](=[O:36])[NH:35][C:29]2=[N:28][CH:27]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 533752283-(3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazoleHCID 666081077'-(2-Methyl-4-(4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazol-3-yl)phenyl)-1'H-spiro[cyclopropane-1,2'-pyrazino[2,3-b]pyrazin]-3'(4'H)-one trifluoroacetateHCID 86644647
7'-bromo-1'H-spiro[cyclopropane-1,2'-pyrazino[2,3-b]pyrazin]-3'(4'H)-one

Produkt 1

HCID 178423523HCID 178423523, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 3776IsopropanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

7′-(2-Methyl-4-(4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazol-3-yl)phenyl)-1′H-spiro[cyclopropane-1,2′-pyrazino[2,3-b]pyrazin]-3′(4′H)-one trifluoroacetate. 3-(3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazole (See Example 2.C) (0.201 g, 0.545 mmol), 7′-bromo-1′H-spiro[cyclopropane-1,2′-pyrazino[2,3-b]pyrazin]-3′(4′H)-one (0.139 g, 0.545 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (0.045 g, 0.054 mmol), sodium carbonate (1 M in water, 1.635 mL, 1.635 mmol), 1,4-dioxane (1.2 mL) and isopropanol (0.4 mL) were combined in a sealable vessel with a stirbar. The system was purged with nitrogen. The resulting mixture was sealed, stirred vigorously and heated at 100° C. for 1 h. The resulting mixture was diluted with water and extracted three times with dichloromethane. The combined organics were concentrated under reduced pressure. The residue was taken up in DMSO and methanol, filtered and purified using reverse-phase preparatory HPLC (20-70% acetonitrile+0.1% TFA in water+0.1% TFA, over 30 min). Fractions containing the desired product were combined and the solvent removed under reduced pressure. The residue was dried under high vacuum to give the desired product (0.109 g, 0.205 mmol, 38% yield) as an orange solid. MS (ESI) m/z 418.4 [M+1]+.

Aufarbeitung

  1. customThe system was purged with nitrogen
  2. customThe resulting mixture was sealed
  3. additionThe resulting mixture was diluted with water
  4. extractionextracted three times with dichloromethane
  5. concentrationThe combined organics were concentrated under reduced pressure
  6. filtrationmethanol, filtered
  7. custompurified
  8. customreverse-phase preparatory HPLC (20-70% acetonitrile+0.1% TFA in water+0.1% TFA, over 30 min)
  9. additionFractions containing the desired product
  10. customthe solvent removed under reduced pressure
  11. customThe residue was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-72f99e94530c403e87467accc13ebd8f
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492381B2

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