Picolinic acid → HCID 70247755, Verbindung

HRID 636286

Reaktionsgleichung

Reaktionsgleichung von HRID 636286
[C:1]1([CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH2:8])[CH:2]=1.[CH:11]1[CH:12]=[CH:13][C:14]2N(O)N=[N:17][C:15]=2[CH:16]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27](O)=[O:28].CN([P+]([O:40]N1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[Na+].[Cl-]>CN(C=O)C.O.CCOC(C)=O>[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([NH:8][CH2:7][C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([CH2:9][NH:10][C:16](=[O:40])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][N:17]=2)[CH:2]=1)=[O:28]

Komponenten

9

Edukt 5

HCID 1018Picolinic acidHCID 5234Sodium ChlorideHCID 151331,3-BenzenedimethanamineHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Produkt 1

HCID 70247755HCID 70247755, VerbindungAusbeute 103,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 1,3-xylylenediamine (132 uL, 1.00 mmol) in DMF (10 mL) was sequentially added IPr2NEt (1.75 mL, 10.0 mmol), HOBt (405 mg, 3.00 mmol), picolinic acid (370 mg, 3.00 mmol) and BOP reagent (1.33 g, 3.00 mmol). After 18 h at room temperature, the reaction mixture was added to a rapidly-stirred mixture of EtOAc (50 mL), H2O (50 mL), and sat'd NaCl (50 mL). After stirring for ca 1 h, the phases were separated and the aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to a brown oil. Purification by flash chromatography (silica gel, EtOAc) afforded 359 mg of the desired product as a white solid. MS (ES+) m/z 347.2 [M+H]+.

Aufarbeitung

  1. customthe phases were separated
  2. extractionthe aqueous layer was extracted with EtOAc (50 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a brown oil
  6. customPurification by flash chromatography (silica gel, EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-80ac522f774a415da7cfb328b872673e
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06191146B1

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