Water → 2-(3-(tert-butylamino)-2-methylpyrido[3,4-b]pyrazin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

HRID 1056247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056247
CC1(C)C(C)(C)OB([C:9]2[NH:17][C:16]3[CH2:15][CH2:14][NH:13][C:12](=[O:18])[C:11]=3[CH:10]=2)O1.[C:20]([NH:24][C:25]1[N:30]=[C:29]2[C:31](Cl)=[N:32][CH:33]=[CH:34][C:28]2=[N:27][C:26]=1[CH3:36])([CH3:23])([CH3:22])[CH3:21].O.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>O1CCOCC1.C(Cl)(Cl)Cl.CC(O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:20]([NH:24][C:25]1[N:30]=[C:29]2[C:31]([C:9]3[NH:17][C:16]4[CH2:15][CH2:14][NH:13][C:12](=[O:18])[C:11]=4[CH:10]=3)=[N:32][CH:33]=[CH:34][C:28]2=[N:27][C:26]=1[CH3:36])([CH3:23])([CH3:22])[CH3:21]

Komponenten

8

Edukt 4

HCID 962WaterHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 89781928N-(tert-butyl)-5-chloro-2-methylpyrido[3,4-b]pyrazin-3-amineHCID 897834962-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-C]pyridin-4-one

Produkt 1

HCID 897833592-(3-(tert-butylamino)-2-methylpyrido[3,4-b]pyrazin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-oneAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittelHCID 21906603Chloroform isopropyl alcoholLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A glass microwave reaction vessel was charged with 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (609) (31 mg, 0.12 mmol) and N-(tert-butyl)-5-chloro-2-methylpyrido[3,4-b]pyrazin-3-amine (15 mg, 0.06 mmol) in 1,4-Dioxane (0.8 mL)/Water (0.2 mL) followed by Xphos (2.8 mg, 6.0 μmol) (Sigma Aldich), Pd2dba3 (2.7 mg, 3.0 μmol) (Strem) and K2PO4 (38 mg, 0.18 mmol) (Sigma Aldich). The reaction mixture was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 100° C. for 1 h. The mixture was diluted with CHCl3/iPrOH (4:1, 30 mL) and washed with water. The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified with prep-TLC (eluted with 8% MeOH in DCM) to give 2-(3-(tert-butylamino)-2-methylpyrido[3,4-b]pyrazin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (5.0 mg, 0.014 mmol, 24% yield) as a light brown solid. MS (ESI, pos. ion) m/z: 351.1 (M+1); 1H NMR (400 MHz, MEOH-D4-d4) δ ppm 8.33 (1H, d, J=5.5 Hz), 7.79 (1H, s), 7.45 (1H, d, J=5.5 Hz), 3.62 (2H, t, J=7.0 Hz), 3.01 (2H, t, J=7.0 Hz), 2.62 (3H, s), 1.70 (9H, s).

Aufarbeitung

  1. customA glass microwave reaction vessel
  2. washwashed with water
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with prep-TLC (eluted with 8% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-494b63ded5ae48488f52e42e909d0a7a
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

Notizen zur Reaktion

Wird geladen…