1-Hydroxybenzotriazole → HCID 58126888, Verbindung

HRID 1971818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1971818
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[CH:17][N:18]([CH2:19][C:20](=[O:27])[N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:12]2=[N:11][C:10]=1[C:28]([OH:30])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:32][CH2:33][C:34](=[O:43])[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+]>C1COCC1>[F:42][C:39]1[CH:38]=[CH:37][C:36]([CH2:35][C:34](=[O:43])[CH2:33][NH:32][C:28]([C:10]2[N:11]=[C:12]3[N:18]([CH2:19][C:20](=[O:27])[N:21]4[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]4)[CH:17]=[CH:16][N:13]3[C:14](=[O:15])[C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:30])=[CH:41][CH:40]=1

Komponenten

7

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 132906742-Propanone, 1-amino-3-(4-fluorophenyl)-, hydrochloride (1:1)HCID 58126863HCID 58126863, Verbindung

Produkt 1

HCID 58126888HCID 58126888, VerbindungAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the product of example 4 (1.0 g, 2.4 mmol) in THF (10 ml) was added compound 1-amino-3-(4-fluoro-phenyl)-propan-2-one hydrochloride (1.0 g, 4.9 mmol), EDCI.HCl (560 mg, 2.9 mmol), HOBt (400 mg, 2.9 mmol) and TEA (1 g, 9.9 mmol) successively at room temperature. The mixture was stirred overnight, after which saturated sodium bicarbonate was added and then extracted with ethyl acetate. The extracts were combined, washed with brine, and then dried over sodium sulfate. The product was purified by column chromatography (CH2Cl2/MeOH=100/1) to give the desired product (540 mg, 40% yield).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe product was purified by column chromatography (CH2Cl2/MeOH=100/1)

Quellen und Nachweise

ORD-Eintrag
ord-40c431fefd6c4a8981a9e75ad16390b1
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431581B2

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