Potassium Phosphate, Tribasic → Ethyl 5-[(tert-butoxycarbonyl)amino]-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate

HRID 2060631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2060631
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12](I)=[N:11][C:10]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:28]2[CH:29]=[CH:30][C:31]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[N:32][CH:33]=2)O1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=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].O1CCOCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:28]2[CH:33]=[N:32][C:31]([N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)=[CH:30][CH:29]=2)=[N:11][C:10]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 67306268Ethyl 5-((tert-butoxycarbonyl)amino)-2-iodothiazole-4-carboxylate

Produkt 1

HCID 67305664Ethyl 5-[(tert-butoxycarbonyl)amino]-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Ethyl 5-[(tert-butoxycarbonyl)amino]-2-iodo-1,3-thiazole-4-carboxylate (1 g, 2.5 mmol), 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]morpholine (1.1 g, 3.7 mmol), Pd2(dba)3 (0.23 g, 0.25 mmol), and tricyclohexylphosphine (0.18 g, 0.63 mmol) were combined in a flask. The flask was evacuated and backfilled with argon three times. Fully degassed dioxane (17 mL) and 1.27 M aqueous potassium phosphate (6.5 ml, 8.3 mmol) were added sequentially. The reaction was heated to 100° C. for 6 h. The mixture was then cooled, diluted with ethyl acetate, washed with water, dried (MgSO4), filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by flash chromatography (silica, 0-75% ethyl acetate/hexanes) to afford the title compound as a yellow solid. LRMS (APCI) calc'd for (C20H27N4O5S) [M+H]+, 435.2; found 435.0.

Aufarbeitung

  1. customThe flask was evacuated
  2. temperatureThe mixture was then cooled
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by flash chromatography (silica, 0-75% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1a16f5ae51f743eeb9fc462ff535fc49
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278335B2

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