Benzyl Isothiocyanate → 6-[(benzylcarbamothioyl)amino]-3-(2-methylpyridin-4-yl)-1H-pyrazolo[4,3-c]pyridin-5-ium trifluoroacetate

HRID 571401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571401
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:12]3[CH:13]=[N:14][C:15]([NH2:17])=[CH:16][C:11]=3[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.[N:37]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[C:38]=[S:39].[C:47]([OH:53])([C:49]([F:52])([F:51])[F:50])=[O:48].C([SiH](CC)CC)C>C1(C)C=CC=CC=1>[F:50][C:49]([F:52])([F:51])[C:47]([O-:53])=[O:48].[CH2:40]([NH:37][C:38]([NH:17][C:15]1[NH+:14]=[CH:13][C:12]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=3)=[N:9][NH:10][C:11]=2[CH:16]=1)=[S:39])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Komponenten

6

Edukt 4

HCID 2346Benzyl IsothiocyanateHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 895258183-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amine2×

Produkt 1

HCID 1176016386-[(benzylcarbamothioyl)amino]-3-(2-methylpyridin-4-yl)-1H-pyrazolo[4,3-c]pyridin-5-ium trifluoroacetateAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of 3-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amine (intermediate 5a; 25 mg, 0.05 mmol) in toluene (1 mL) was treated with (isothiocyanatomethyl)benzene (15 mg, 0.1 mmol) and the mixture was heated at 100° C. overnight. The volatiles were concentrated in vacuo and the residue was directly dissolved in DCM (0.8 mL), treated with TFA (0.2 mL) and triethylsilane (0.008 mL, 0.051 mmol) and left under stirring for 5 h, then concentrated in vacuo and purified by MS-directed reverse phase preparative-HPLC (C-18 stationary phase, eluting with a H2O/MeCN gradient with 0.1% TFA) to yield 6-[(benzylcarbamothioyl)amino]-3-(2-methylpyridin-4-yl)-1H-pyrazolo[4,3-c]pyridin-5-ium trifluoroacetate as a yellow solid (7 mg, 0.014 mmol, 27%). MS ESI calc'd. for C20H19N6S [M+1]+ 375, found 375.

Aufarbeitung

  1. concentrationThe volatiles were concentrated in vacuo
  2. dissolutionthe residue was directly dissolved in DCM (0.8 mL)
  3. waitleft
  4. concentrationconcentrated in vacuo
  5. custompurified by MS-directed reverse phase preparative-HPLC (C-18 stationary phase
  6. washeluting with a H2O/MeCN gradient with 0.1% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-77265b85697b4309aa0698e1e7d5f137
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023865B2

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