Chlorotrimethylsilane → 2-[4-(4H-1,2,4-triazol-4-yl)phenyl]acetic acid

HRID 495078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 495078
[CH:1]([NH:3][NH:4][CH:5]=O)=O.C[Si](Cl)(C)C.CCN(CC)CC.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([OH:29])=[O:28])=[CH:22][CH:21]=1>N1C=CC=CC=1>[N:4]1[N:3]=[CH:1][N:19]([C:20]2[CH:21]=[CH:22][C:23]([CH2:26][C:27]([OH:29])=[O:28])=[CH:24][CH:25]=2)[CH:5]=1

Komponenten

6

Edukt 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 123421,2-HydrazinedicarboxaldehydeHCID 145334-Aminophenylacetic acid

Produkt 1

HCID 204742832-[4-(4H-1,2,4-triazol-4-yl)phenyl]acetic acidAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Adapting a protocol by Catarzi et al (J. Med Chem., 2001, 44, 3157-3165), diformylhydrazine (352 mg, 4.0 mmol) and then dropwise trimethylsilyl chloride (2.53 mL, 20 mmol) and Et3N (1.30 mL, 9.3 mmol) were added to a suspension of 4-aminophenylacetic acid (201 mg, 1.33 mmol) in anhydrous pyridine. The mixture was heated at 100° C. overnight, volatiles were removed at reduced pressure and the resulting solid was treated with water (6 mL), collected, washed with H2O and dried in vacuo to provide 251 mg (93%) of 141JP01 as a light brown solid. LCMS m/z 204[M+H]+. 1H-NMR (DMSO-d6) δ 9.05 (s, 2H), 7.62 (d, 1H, J=8.6), 7.40 (d, 1H, J=8.2), 3.61 (s, 2H).

Aufarbeitung

  1. customvolatiles were removed at reduced pressure
  2. additionthe resulting solid was treated with water (6 mL)
  3. customcollected
  4. washwashed with H2O
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6267f57b78b647638a0b71b7ea7f113d
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538222B2

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