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Cesium carbonate → 6-Trifluoromethyl-pyridine-2-carboxylic acid[6-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-pyrimidin-4-yl]-amide

HRID 1486749
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1486749
[C:1]([NH:5][C:6]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][B-](F)(F)F)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:20]1[N:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[N:30]=2)=[O:28])[CH:21]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([NH:5][C:6]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:20]2[N:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:36])([F:38])[F:37])[N:30]=3)=[O:28])[CH:21]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl2×HCID 867065656-Trifluoromethyl-pyridine-2-carboxylic acid (6-chloro-pyrimidin-4-yl)-amideHCID 131736817((4-(Tert-butylcarbamoyl)piperidin-1-yl)methyl)trifluoroborate

Produkt 1

HCID 118521926
6-Trifluoromethyl-pyridine-2-carboxylic acid[6-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-pyrimidin-4-yl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 21881883Oxolane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of ((4-(tert-butylcarbamoyl)piperidin-1-yl)methyl)trifluoroborate (45 mg, 0.169 mmol) in THF/water 4:1 (3 mL) are added 6-trifluoromethyl-pyridine-2-carboxylic acid (6-chloro-pyrimidin-4-yl)-amide (51.2 mg, 0.169 mmol), palladium (II) acetate, (0.949 mg, 0.00423 mmol,), X-Phos, (2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl) (4.84 mg, 0.0101 mmol) and Cs2CO3, (165 mg, 0.507 mmol). The mixture is purged with argon and is stirred overnight in a sealed tube at 80° C. The mixture is let to cool down. Water (3 mL) and AcOEt (5 mL) are added and the aqueous phase is extracted with AcOEt (10 mL). The organic phase is dried over MgSO4, filtered and evaporated. The residue is purified by prep HPLC E delivering the title compound (27 mg, 30%) as a white powder, LC-MS A: tR=0.74 min; [M+H]+=465.4.

Aufarbeitung

  1. customThe mixture is purged with argon
  2. temperatureto cool down
  3. additionWater (3 mL) and AcOEt (5 mL) are added
  4. extractionthe aqueous phase is extracted with AcOEt (10 mL)
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by prep HPLC E

Quellen und Nachweise

ORD-Eintrag
ord-7a928ac18881410ab4577b4524703fce
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09428456B2

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