Cyclohexanecarbonyl chloride → Cyclohexanecarboxylic acid [2-(4-nitro-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide

HRID 854082

Reaktionsgleichung

Reaktionsgleichung von HRID 854082
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:19][C:13]3[CH:14]=[N:15][C:16]([NH2:18])=[CH:17][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:20]1([C:26](Cl)=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C1COCC1.N1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:19][C:13]3[CH:14]=[N:15][C:16]([NH:18][C:26]([CH:20]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]4)=[O:27])=[CH:17][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 589329182-(4-Nitro-phenyl)-3H-imidazo[4,5-c]pyridine-6-ylamine

Produkt 1

HCID 58932915Cyclohexanecarboxylic acid [2-(4-nitro-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amideAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirring solution of 8 (0.116 g, 0.45 mmol) in dry THF and Pyridine (10 ml/0.300 ml), cyclohexanecarbonyl chloride (0.100 ml, 0.68 mmol) was added and stirred at room temperature for 4 h. The reaction was quenched by the addition of water and the yellow solid was filtered, air-dried and dissolved in EtOAc and passed through a bed of SiO2 gel. Elution with EtOAc afforded the desired product 9 (0.095 g, 58%). 1H NMR (DMSO-d6, 500 MHz): δ 13.49 (1H, s), 10.38 (1H, s, NH), 8.76 (1H, s), 8.41 (4H, dd, J=15 and 5 Hz); 8.34 (1H, s), 2.53 (1H, m), 1.80-1.20 (10, m); MS m/z: 366 (M+1), 364 (M−1). The product was used for the next step.

Aufarbeitung

  1. customThe reaction was quenched by the addition of water
  2. filtrationthe yellow solid was filtered
  3. customair-dried
  4. dissolutiondissolved in EtOAc
  5. washElution with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-c1f220b9194d4aab9201611720c59b5e
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07256287B2

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