Trifluoroacetic acid → HCID 58025821, Verbindung

HRID 1046943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1046943
C(O[C:6]([NH:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=1)=[S:11])=[O:7])(C)(C)C.C(OC(NNC(=O)C1C=CC(F)=CC=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.CCN(C(C)C)C(C)C.[F:53][CH:54]([F:64])[O:55][C:56]1[CH:63]=[CH:62][CH:61]=[CH:60][C:57]=1[CH:58]=O.[F:65][C:66]1[CH:74]=[C:73]([F:75])[CH:72]=[C:71]([F:76])[C:67]=1C(Cl)=O>C(Cl)Cl>[F:53][CH:54]([F:64])[O:55][C:56]1[CH:63]=[CH:62][CH:61]=[CH:60][C:57]=1[CH:58]1[N:8]([C:6]([C:67]2[C:66]([F:65])=[CH:74][C:73]([F:75])=[CH:72][C:71]=2[F:76])=[O:7])[N:9]=[C:10]([C:12]2[CH:13]=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[S:11]1

Komponenten

8

Edukt 6

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 1448952,4,6-Trifluorobenzoyl chlorideHCID 27369842-(Difluoromethoxy)benzaldehydeHCID 67279032tert-Butyl 2-(4-fluorobenzoyl)hydrazine-1-carboxylateHCID 86637598HCID 86637598, Verbindung

Produkt 1

HCID 58025821HCID 58025821, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N′-(6-Methyl-pyridine-3-carbothioyl)-hydrazinecarboxylic acid tert-butyl ester (0.1 mmol) prepared as described in example 3 for N′-(4-fluoro-benzoyl)-hydrazinecarboxylic acid tert-butyl ester, is treated with TFA (1 mmol) in dry CH2Cl2 (1 mL) at room temperature for 30 minutes. Solvent is removed and the residue is dissolved in dry CH2Cl2 (1 mL). DIEA (0.287 mmol) is added to the solution and the mixture is treated with 2-difluoromethoxy-benzaldehyde (0.12 mmol) in the presence of 4 Å molecular sieves. 2,4,6-Trifluorobenzoyl chloride (0.15 mmol) is added after 5 minutes. The mixture is kept at ambient temperature for 16 hours and purified by preparative HPLC (20-100% MeCN/H2O) to yield [2-(2-difluoromethoxy-phenyl)-5-(6-methyl-pyridin-3-yl)-[1,3,4]thiadiazol-3-yl]-(2,4,6-trifluoro-phenyl)-methanone: 1H NMR (400 MHz, CDCl3) 8.71 (d, J=2.1 Hz, 1H), 7.81 (dd, J1=8.2 Hz, J2=2.2 Hz, 1H), 7.53 (s, 1H), 7.36-7.4 (m, 2H), 7.26 (d, J=8.1 Hz, 2H), 7.18 (d, J=8.3 Hz, 1H), 6.78 (t, J=8.3 Hz, 2H), 6.67 (dd, J1=75.0 Hz, J2=71.7 Hz, 1H), 2.64 (s, 3H); LC/MS (ES+): (M+1) 480.1.

Aufarbeitung

  1. customSolvent is removed
  2. dissolutionthe residue is dissolved in dry CH2Cl2 (1 mL)
  3. custompurified by preparative HPLC (20-100% MeCN/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-877c62aef0df40468ee919ee45fabe54
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569345B2

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