Sodium Hydroxide → (6-Chloro-5-cyclopropylmethoxy-pyridin-2-yl)-(2,2-dimethyl-pyrrolidin-1-yl)-methanone

HRID 624910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624910
C1(CO[C:6]2[N:11]=[C:10]([C:12](O)=O)[CH:9]=[CH:8][C:7]=2OC(F)(F)F)CC1.[Cl:20][C:21]1[N:26]=[C:25]([C:27]([OH:29])=O)[CH:24]=[CH:23][C:22]=1[O:30][CH2:31][CH:32]1[CH2:34][CH2:33]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.CC1(C)CCCN1.[OH-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Cl:20][C:21]1[N:26]=[C:25]([C:27]([N:11]2[CH2:6][CH2:7][CH2:8][C:10]2([CH3:9])[CH3:12])=[O:29])[CH:24]=[CH:23][C:22]=1[O:30][CH2:31][CH:32]1[CH2:34][CH2:33]1

Komponenten

9

Edukt 6

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 4147732,2-DimethylpyrrolidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 902025746-Cyclopropylmethoxy-5-trifluoromethoxy-pyridine-2-carboxylic acidHCID 902026096-Chloro-5-cyclopropylmethoxy-pyridine-2-carboxylic acid

Produkt 1

HCID 76284104(6-Chloro-5-cyclopropylmethoxy-pyridin-2-yl)-(2,2-dimethyl-pyrrolidin-1-yl)-methanoneAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The mixture of 6-cyclopropylmethoxy-5-trifluoromethoxy-pyridine-2-carboxylic acid and 6-chloro-5-cyclopropylmethoxy-pyridine-2-carboxylic acid (Example 47 a, 50 mg, 180 μmol) was dissolved in DMF (2 mL). TBTU (63.7 mg, 198 μmol), DIEA (154 μl, 902 μmol) and 2,2-dimethylpyrrolidine (CAN 35018-15-6, 24 μl, 198 μmol) were added and the reaction mixture was stirred at room temperature for 16 hours. Ethyl acetate (3 mL) and 1 N sodium hydroxide solution (2 mL) were added; the mixture was dried by passage through ChemElut® and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, ethyl acetate/n-heptane gradient) to give the title compound (17 mg, 31%) as off-white wax; LC-MS (UV peak area, ESI) 97%, 309.1367 [MH+].

Aufarbeitung

  1. customthe mixture was dried by passage through ChemElut®
  2. concentrationconcentrated in vacuo
  3. customThe crude material was purified by flash chromatography (silica gel, ethyl acetate/n-heptane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-069ed15813574becafea87d0a5e29011
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303012B2

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