Triethylamine → HCID 67214304, Verbindung

HRID 2420761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2420761
CCCP(=O)=O.[CH3:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=1[NH:17][C:18]1[N:23]=[C:22]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:20][N:19]=1.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([N:39]2[CH2:40][CH2:41][N:36]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=3)[CH2:37][CH2:38]2)=[O:14])=[CH:10][C:9]=1[NH:17][C:18]1[N:23]=[C:22]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:20][N:19]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 944591-(2-Pyridyl)piperazineHCID 516892Sodium BicarbonateHCID 104028804-Methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acidHCID 16167369Propylphosphoric anhydride

Produkt 1

HCID 67214304HCID 67214304, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution containing ˜50% of propylphosphonic anhydride in N,N-dimethylformamide (Fluka, Buchs, Switzerland; 674 μL, ˜1 mmol) is added within 20 minutes to a stirred mixture of 4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-benzoic acid (214.4 mg, 0.7 mmol), 1-(2-pyridyl)piperazine (Aldrich, Buchs, Switzerland; 114.3 mg, 0.7 mmol) and triethylamine (776 μL, 5.6 mmol) in 2 mL N,N-dimethylformamide. After stirring for 24 hours at room temperature, the mixture is treated with a half-saturated aqueous solution of sodium hydrogen carbonate and extracted three times with ethyl acetate. The solvent is evaporated off under reduced pressure and the residue dried in vacuo. The crude product is purified by column chromatography on silica gel, eluent 5-10% methanol in dichloromethane, to give the title compound as a solid. 1H-NMR (400 MHz, DMSO-d6, δ): 2.31 (s, 3H); 3.35-3.74 (m, 8H); 6.65 (ddd, 1H); 6.79 (d, 1H); 7.13 (dd, 1H); 7.32 (d, 1H); 7.44 (d, 1H); 7.49-7.56 (m, 2H); 7.69 (m, 1H); 8.11 (m, 1H); 8.40 (m, 1H); 8.52 (d, 1H); 8.66 (dd, 1H); 9.06 (s, 1H); 9.24 (m, 1H).

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. customThe solvent is evaporated off under reduced pressure
  3. customthe residue dried in vacuo
  4. customThe crude product is purified by column chromatography on silica gel, eluent 5-10% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-ebf1f770d2774bf282a15f3708a44051
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07956053B2

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