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Potassium Phosphate, Tribasic → tert-butyl 4-(4-amino-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1615467
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1615467
Br[C:2]1[N:10]2[C:5]([C:6]([NH2:11])=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.CC1(C)C(C)(C)OB([C:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH:29]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:11][C:6]1[C:5]2=[CH:4][C:3]([CH2:12][CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:2]([C:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH:29]=3)[N:10]2[N:9]=[CH:8][N:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 666123207-Bromo-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Produkt 1

HCID 66601711tert-butyl 4-(4-amino-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5,6-dihydropyridine-1(2H)-carboxylateAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of the compound (135 mg, 0.42 mmol) prepared in Example 13, tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (194 mg, 0.63 mmol), potassium phosphate (2N, 1 mL, 2.0 mmol), Pd(PPh3)4 (11 mg, 0.01 mmol) in dioxane (3 mL) was deoxygenated by nitrogen gas for 5 minutes, and the reactor was sealed, heated at 90° C. for 20 hours. The mixture was concentrated, extracted with DCM and sodium hydroxide (1N). The organic layer was dried, concentrated, and the crude product was purified by prep TLC using 5% methanol in DCM (with 1% ammonium hydroxide) to obtain the title compound (132 mg) having the following physical data.

Aufarbeitung

  1. customthe reactor was sealed
  2. concentrationThe mixture was concentrated
  3. extractionextracted with DCM and sodium hydroxide (1N)
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customthe crude product was purified by prep TLC

Quellen und Nachweise

ORD-Eintrag
ord-d1ebbaae2d654fa1a8463d09dcd1dc8e
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08765754B2

Notizen zur Reaktion

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