Potassium Phosphate, Tribasic → HCID 24983905, Verbindung

HRID 1014700

Reaktionsgleichung

Reaktionsgleichung von HRID 1014700
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26]C)=[O:25])=[CH:19][CH:18]=4)[N:15]=3)[NH:10][C:9]2=[O:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC1(C)C(C)(C)OB(C2C=CC(CC(OC)=O)=CC=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O.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]>[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([C:17]4[CH:18]=[CH:19][C:20]([CH2:23][C:24]([OH:26])=[O:25])=[CH:21][CH:22]=4)[N:15]=3)[NH:10][C:9]2=[O:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 11219601Methyl 2-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetateHCID 66699783HCID 66699783, Verbindung

Produkt 1

HCID 24983905HCID 24983905, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Methyl 2-(4-(3-(cyclohexylmethyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)phenyl)acetate. Bromo-1-(cyclohexylmethyl)-4-imidazolino[4,5-b]pyrazin-2-one (200 mg, 0.64 mmol), methyl 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate (213 mg, 0.77 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane (53 mg, 0.06 mmol) and potassium phosphate (543 mg, 2.56 mmol) in DMF (20 mL) and water (5 mL) were reacted according to General Procedure B. The product was purified by reverse-phase semi-preparatory HPLC (30-100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). The desired fractions were concentrated, and the residue was taken up in DMSO (2 mL) and heated at 100° C. until completely dissolved. Water was added upon cooling and the desired product precipitated out of solution. The precipitate was collected by vacuum filtration, washed with water and dried under high vacuum to provide the title compound (95 mg, 39 yield) as a tan solid. MS (ESI) m/z 381.4 [M+1]+.

Aufarbeitung

  1. customThe product was purified by reverse-phase semi-preparatory HPLC (30-100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min)
  2. concentrationThe desired fractions were concentrated
  3. dissolutionuntil completely dissolved
  4. additionWater was added
  5. temperatureupon cooling
  6. customthe desired product precipitated out of solution
  7. filtrationThe precipitate was collected by vacuum filtration
  8. washwashed with water
  9. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-173cc5138b574c71b156a30d32726433
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981893B2

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