Diisopropylethylamine → HCID 178461813, Verbindung

HRID 20546

Reaktionsgleichung

Reaktionsgleichung von HRID 20546
[OH:1][CH2:2][C@H:3]([CH3:29])[O:4][C:5]1[CH:6]=[C:7]([CH:18]=[C:19]([C:21]([NH:23][C:24]2[CH:28]=[CH:27][NH:26][N:25]=2)=[O:22])[CH:20]=1)[O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1.CN(C(ON1N=NC2C=[CH:42][CH:43]=[N:44][C:39]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.N1CCC1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[N:44]1([C:13]([C:12]2[CH:11]=[CH:10][C:9]([O:8][C:7]3[CH:18]=[C:19]([CH:20]=[C:5]([O:4][C@@H:3]([CH3:29])[CH2:2][OH:1])[CH:6]=3)[C:21]([NH:23][C:24]3[CH:28]=[CH:27][NH:26][N:25]=3)=[O:22])=[CH:17][CH:16]=2)=[O:15])[CH2:43][CH2:42][CH2:39]1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12308726Azetidine hydrochlorideHCID 178461815HCID 178461815, Verbindung

Produkt 1

HCID 178461813HCID 178461813, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 4-{3-[(1S)-2-hydroxy-1-methylethoxy]-5-[(1H-pyrazol-3-ylamino)carbonyl]phenoxy}benzoic acid (130 mg, 0.327 mmol), HATU (156 mg, 0.41 mmol), azetidine hydrochloride (38 mg, 0.41 mmol) and DIPEA (0.143 mL; 0.82 mmol) in DMF (2 mL) was stirred at ambient temperature for 16 hours. Water was added to the reaction mixture and it was extracted into ethyl acetate (3×30 mL). The organic phases were combined, washed with brine solution and dried (MgSO4). The filtrate was concentrated in vacuo and the residue chromatographed, eluting with 0-50% methanol in DCM, to give a clear oil which gave a foam under high vacuum (65 mg, 46%).

Aufarbeitung

  1. extractionwas extracted into ethyl acetate (3×30 mL)
  2. washwashed with brine solution
  3. dry with materialdried (MgSO4)
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue chromatographed
  6. washeluting with 0-50% methanol in DCM
  7. customto give a clear oil which
  8. customgave a foam under high vacuum (65 mg, 46%)

Quellen und Nachweise

ORD-Eintrag
ord-56ffacba82354ea1b1d9132faf8ddbd8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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