Triethylamine → 1-(1-{[4-(Pyridin-2-yloxy)phenyl]carbonyl}azetidin-3-yl)-4-(1,3-thiazol-2-ylcarbonyl)piperazine

HRID 401675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401675
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1.[NH:17]1[CH2:20][CH:19]([N:21]2[CH2:26][CH2:25][N:24]([C:27]([C:29]3[S:30][CH:31]=[CH:32][N:33]=3)=[O:28])[CH2:23][CH2:22]2)[CH2:18]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>O.CN(C=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([N:17]2[CH2:18][CH:19]([N:21]3[CH2:22][CH2:23][N:24]([C:27]([C:29]4[S:30][CH:31]=[CH:32][N:33]=4)=[O:28])[CH2:25][CH2:26]3)[CH2:20]2)=[O:14])=[CH:15][CH:16]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222620524-(Pyridin-2-yloxy)benzoic acidHCID 59625677(4-(Azetidin-3-yl)piperazin-1-yl)(thiazol-2-yl)methanone

Produkt 1

HCID 596257441-(1-{[4-(Pyridin-2-yloxy)phenyl]carbonyl}azetidin-3-yl)-4-(1,3-thiazol-2-ylcarbonyl)piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 44c (60 mg, 0.28 mmol), 5e (105 mg, 0.36 mmol), HATU (159 mg, 0.42 mmol), Et3N (1 mL), and DMF (3 mL) was stirred at room temperature overnight, and then poured into water (10 mL). The mixture was extracted with EtOAc. The extracts were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography (silica gel, 7% MeOH/CH2Cl2) to give 98 mg of Cpd 913. MS m/z (M+H+) 450.0.

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc
  2. washThe extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica gel, 7% MeOH/CH2Cl2)
  6. customto give 98 mg of Cpd 913

Quellen und Nachweise

ORD-Eintrag
ord-8b5b7fc00b284914a6daf19f6b8b8baf
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741887B2

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