2-(Piperidin-1-yl)aniline → 5-Cyano-1H-pyrrole-2-carboxylic Acid (2-piperidin-1-yl-phenyl)-amide

HRID 32885

Reaktionsgleichung

Reaktionsgleichung von HRID 32885
[C:1]([C:3]1[NH:7][C:6]([C:8]([OH:10])=O)=[CH:5][CH:4]=1)#[N:2].Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.[N:33]1([C:39]2[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=2[NH2:41])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>ClCCl.[Cl-].[Na+].O>[N:33]1([C:39]2[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=2[NH:41][C:8]([C:6]2[NH:7][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[O:10])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Komponenten

7

Edukt 4

HCID 4587952-(Piperidin-1-yl)anilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 553027535-cyano-1H-pyrrole-2-carboxylic acidHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 116737515-Cyano-1H-pyrrole-2-carboxylic Acid (2-piperidin-1-yl-phenyl)-amideAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To 24.5 mg (0.180 mmol) 5-cyano-1H-pyrrole-2-carboxylic acid (as prepared in the previous step) in dichloromethane (10 mL) was added 53 mg (0.28 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI), hydroxybenzotriazole (HOBt, 30 mg, 0.22 mmol), and 2-piperidinoaniline (38 mg, 0.22 mmol) and the mixture stirred for 6.5 h at RT. The mixture was poured into brine (50 mL) and extracted with dichloromethane (3×20 mL). The organic layers were washed with brine (20 mL), dried over Na2SO4 and the solvent was removed in vacuo. Purification of the resulting residue by silica gel preparative TLC eluting with 30% ethyl acetate in hexane yielded 24 mg (42%) of the title compound as a brown solid. 1H-NMR (400 MHz, CDCl3): δ 11.90 and 10.45 (br s, 1H, rotomers), 9.60 and 9.38 (s, 1H, rotomers), 8.60 and 8.47 (d, 1H, J=7.9 Hz, rotomers), 7.29-6.74 (m, 5H), 2.85 (m, 4H), 1.78-1.68 (m, 6H). LC-MS (ESI, m/z): Calcd. for C17H19N4O, 295.2 (M+H); found: 295.2.

Aufarbeitung

  1. extractionextracted with dichloromethane (3×20 mL)
  2. washThe organic layers were washed with brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed in vacuo
  5. customPurification of the resulting residue by silica gel preparative TLC
  6. washeluting with 30% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-d32e9458d66e40388d376036b40b4567
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427683B2

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