Potassium Carbonate → N-[1-(2-Cyclopropyl-1-methylethyl)piperidin-4-yl]-6-(3-fluorophenyl)nicotinamide

HRID 602087

Reaktionsgleichung

Reaktionsgleichung von HRID 602087
[CH:1]1([CH2:4][C:5](=O)[CH3:6])[CH2:3][CH2:2]1.[F:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:29]=[CH:28][C:18]([C:19]([NH:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[O:20])=[CH:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[K+].[K+]>C(O)C.C(O)(=O)C.CS(C)=O.C1COCC1>[CH:1]1([CH2:4][CH:5]([N:25]2[CH2:24][CH2:23][CH:22]([NH:21][C:19](=[O:20])[C:18]3[CH:28]=[CH:29][C:15]([C:11]4[CH:12]=[CH:13][CH:14]=[C:9]([F:8])[CH:10]=4)=[N:16][CH:17]=3)[CH2:27][CH2:26]2)[CH3:6])[CH2:3][CH2:2]1

Komponenten

9

Edukt 4

HCID 11430Potassium CarbonateHCID 5370251-Cyclopropylpropan-2-oneHCID 5049666Sodium triacetoxyborohydrideHCID 672679066-(3-fluorophenyl)-N-(piperidin-4-yl)nicotinamide

Produkt 1

HCID 59743699N-[1-(2-Cyclopropyl-1-methylethyl)piperidin-4-yl]-6-(3-fluorophenyl)nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 679Dimethyl SulfoxideLösungsmittelHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-cyclopropylpropan-2-one (0.2 mL, 0.08 mmol in 1:1 THF:DMSO) was added 6-(3-fluorophenyl)-N-(piperidin-4-yl)nicotinamide (in 1:1 THF:DMSO, 0.2 mL, 0.08 mmol), sodium triacetoxyborohydride dispersion (0.33 mL, 2.5 eq, in 1:1 THF:DMSO) and glacial acetic acid (0.01 mL). The reaction mixture was stirred at room temperature for 16-24 h and then aqueous K2CO3 (3 M, 0.2 mL) and ethanol (0.55 mL) was added. The reaction was shaken for 30 min and then the mixture was filtered and the filtrate concentrated and the residue purified by RP-HPLC to give the desired product. LC/MS=382.4 (M+H) observed, 382.23 expected.

Aufarbeitung

  1. stirringThe reaction was shaken for 30 min
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate concentrated
  4. customthe residue purified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3768ad9dae2347b9ab440a2bbb884ccf
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902373B2

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