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Pyridine → HCID 58017523, Verbindung

HRID 1642760
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1642760
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:28]2[CH:32]=[N:31][N:30]=[N:29]2)=[C:6]([CH2:8][NH:9][C:10]([C@@H:12]2[CH2:16][CH:15]=[N:14][N:13]2[C:17](=[O:27])[C@@H:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[OH:19])=[O:11])[CH:7]=1.N1C=CC=CC=1.[C:39](Cl)(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:39]([O:19][C@H:18]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:17]([N:13]1[C@H:12]([C:10](=[O:11])[NH:9][CH2:8][C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:28]2[CH:32]=[N:31][N:30]=[N:29]2)[CH2:16][CH:15]=[N:14]1)=[O:27])(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 1049Pyridine2×HCID 7412Benzoyl chloride3×HCID 44537923AZ-12971554

Produkt 1

HCID 58017523HCID 58017523, VerbindungAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a mixture of (3S)—N—[[5-chloro-2-(tetrazol-1-yl)phenyl]methyl]-2-[(2R)-2-(4-fluorophenyl)-2-hydroxy-acetyl]-3,4-dihydropyrazole-3-carboxamide (0.48 g, 1.05 mmol), pyridine (6 mL, 74 mmol), and DMAP (0.023 g, 0.188 mmol) in CH2Cl2 (8 mL) at −10° C. was added benzoyl chloride (135 μL, 1.15 mmol). The reaction mixture was allowed to attain rt and was stirred for 5 h. Another portion of benzoyl chloride (400 μL, 3.4 mmol) was added. The mixture was stirred for 60 h. LCMS analysis indicated only a trace amount of product. The solvents were removed by evaporation and pyridine (5 mL, 62 mmol) was added followed by another portion of benzoyl chloride (400 μL, 3.4 mmol). The reaction mixture was heated to 70° C. overnight. LCMS analysis indicated approximately 20% conversion of starting material. The solvent was evaporated of and the residue was purified by HPLC (MeCN gradient 0 to 100% in 0.1 M NH4OAc buffer containing 5% MeCN). The relevant fractions were combined and lyophilized to give the title compound (77 mg, 13%) together with 289 mg of unreacted starting material.

Aufarbeitung

  1. customto attain rt
  2. stirringThe mixture was stirred for 60 h
  3. additionwas added
  4. customThe solvent was evaporated of and the residue
  5. customwas purified by HPLC (MeCN gradient 0 to 100% in 0.1 M NH4OAc buffer containing 5% MeCN)

Quellen und Nachweise

ORD-Eintrag
ord-7103c96fb96a4883bd08c65010c5781c
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08119673B2

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