4-chloro-1-methyl-1H-pyrazole-5-carboxylic acid → HCID 51034816, Verbindung

HRID 908207

Reaktionsgleichung

Reaktionsgleichung von HRID 908207
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Cl:23][C:24]1[CH:28]=[N:27][N:26]([CH3:29])[C:25]=1[C:30]([OH:32])=O.[C:33]1([C:39]2[N:40]=[C:41]3[CH:46]=[C:45]([NH2:47])[CH:44]=[CH:43][N:42]3[CH:48]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C.C(OCC)(=O)C>[C:33]1([C:39]2[N:40]=[C:41]3[CH:46]=[C:45]([NH:47][C:30]([C:25]4[N:26]([CH3:29])[N:27]=[CH:28][C:24]=4[Cl:23])=[O:32])[CH:44]=[CH:43][N:42]3[CH:48]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Komponenten

6

Edukt 3

HCID 6708234-chloro-1-methyl-1H-pyrazole-5-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 569555022-Phenylimidazo[1,2-a]pyridin-7-amine

Produkt 1

HCID 51034816HCID 51034816, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under an atmosphere of nitrogen, N—N-diisopropylethylamine (749 mg, 6 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU, 744 mg, 1.94 mmol) were added to a solution of 4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid (310 mg, 1.94 mmol, Art-Chem B000148) in DMF (5 ml). After 30 min, 2-phenyl-imidazo[1,2-a]pyridin-7-ylamine (404 mg, 1.94 mmol) was added, and the brown solution was stirred over the weekend (r.t.). The reaction mixture was taken up in ethyl acetate and washed with water. After drying (Na2SO4), the solvent was evaporated and the title compound (170 mg, 25%) was isolated by column chromatography (silica gel, heptane:ethyl acetate=100:0-50:50). MS (m/e)=352.2 [M+H+].

Aufarbeitung

  1. washwashed with water
  2. dry with materialAfter drying (Na2SO4)
  3. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-119376ba09d94afdbe94c2a1ae19e3e1
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017604B2

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