Diisopropylethylamine → HCID 51035143, Verbindung

HRID 2382754

Reaktionsgleichung

Reaktionsgleichung von HRID 2382754
C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[CH:15]=[N:14][N:13]([CH3:16])[C:12]=1[C:17]([OH:19])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:42]1([C:48]2[N:49]=[C:50]3[CH:55]=[C:54]([NH2:56])[N:53]=[CH:52][N:51]3[CH:57]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C=O)C>[C:42]1([C:48]2[N:49]=[C:50]3[CH:55]=[C:54]([NH:56][C:17]([C:12]4[N:13]([CH3:16])[N:14]=[CH:15][C:11]=4[Cl:10])=[O:19])[N:53]=[CH:52][N:51]3[CH:57]=2)[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 4040512-Phenylimidazo[1,2-c]pyrimidin-7-amineHCID 6708234-chloro-1-methyl-1H-pyrazole-5-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Produkt 1

HCID 51035143HCID 51035143, VerbindungAusbeute 6,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DMF (8 ml) and diisopropylethylamine (738 mg) were added to 4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid (916 mg, 5.7 mmol) and TBTU (1.83 g), and the mixture was stirred at r.t. (10 min). 2-Phenyl-imidazo[1,2-c]pyrimidin-7-ylamine (400 mg, 1.9 mmol) was added and the mixture was stirred at r.t. overnight. The reaction mixture was then poured on water (35 ml), and the mixture was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and evaporated. The title compound (45 mg, 6.7%) was isolated from the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-60:40), followed by preparative, inverse-phase HPLC (Agilent Zorbax XdB-C18 column, time per run ˜7 min, flow rate 30 ml/min, solvent gradient H2O/CH3CN=95:5-5:95). MS (m/e)=353.1 [M+H+].

Aufarbeitung

  1. stirringthe mixture was stirred at r.t. overnight
  2. additionThe reaction mixture was then poured on water (35 ml)
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e7b41f95976440fc90cb5b336dc1263e
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263584B2

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