1,2-Dichloroethane → HCID 66677906, Verbindung

HRID 1951950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1951950
[CH2:1]([C:3]1[C:4]([C:14]([OH:16])=O)=[N:5][O:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:2].[Na].C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.C(Cl)CCl.O[N:42]=[C:43]([C:45]1[CH:62]=[CH:61][C:48]([CH2:49][N:50]2[CH2:53][CH:52]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:51]2)=[CH:47][CH:46]=1)[NH2:44].N1C=CC=CC=1C1C(C(F)(F)F)=C(C2ON=C(C3C=CC(CN4CC(C(O)=O)C4)=CC=3)N=2)ON=1>C(#N)C>[CH2:1]([C:3]1[C:4]([C:14]2[O:16][N:44]=[C:43]([C:45]3[CH:46]=[CH:47][C:48]([CH2:49][N:50]4[CH2:51][CH:52]([C:54]([O:56][C:57]([CH3:58])([CH3:60])[CH3:59])=[O:55])[CH2:53]4)=[CH:61][CH:62]=3)[N:42]=2)=[N:5][O:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:2]

Komponenten

9

Edukt 7

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5360545SodiumHCID 468359141-(4-(5-(3-(Pyridin-2-yl)-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acidHCID 580628464-Ethyl-5-(pyridin-2-yl)isoxazole-3-carboxylic acidHCID 76806751tert-butyl 1-[[4-(N'-hydroxycarbamimidoyl)phenyl]methyl]azetidine-3-carboxylate

Produkt 1

HCID 66677906HCID 66677906, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-ethyl-5-(pyridin-2-yl)isoxazole-3-carboxylic acid, sodium salt (22 mg), HOBt (27.8 mg, 0.181 mmol), and diisopropylethylamine (0.070 mL, 0.403 mmol) in acetonitrile (1 mL) was added EDC (45.4 mg, 0.237 mmol) and tert-butyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate, Int. 1 (30.8 mg, 0.101 mmol). The reaction mixture was stirred at 80° C. for 4 h. and then concentrated under reduced pressure. The residue was diluted with ethyl acetate (3 mL), washed with a saturated aqueous solution of sodium bicarbonate, washed with water (1 mL), washed with brine (1 mL), and dried over anhydrous sodium sulfate. Concentration followed by purification by preparative HPLC [Prep HPLC: Column: PHENOMENEX® S10 30×100 mm; Gradient time: 10 min; Flow rate=40 ml/min; Solvent A=10% MeOH—90% Water—0.1% TFA; Solvent B=90% MeOH—10% water—0.1% TFA; Start % B=20; Final % B=100.] afforded tert-butyl 1-(4-(5-(4-ethyl-5-(pyridin-2-yl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate (3 mL)
  3. washwashed with a saturated aqueous solution of sodium bicarbonate
  4. washwashed with water (1 mL)
  5. washwashed with brine (1 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationConcentration
  8. customfollowed by purification by preparative HPLC [Prep HPLC
  9. custom10 min

Quellen und Nachweise

ORD-Eintrag
ord-ab502ad3b1e64b228a050954f9f90c4d
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404672B2

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