Triethylamine → HCID 54167831, Verbindung

HRID 133595

Reaktionsgleichung

Reaktionsgleichung von HRID 133595
C(N(CC)CC)C.[C:8]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=O)#[N:9].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:40][C:41]1[CH:62]=[CH:61][C:44]([CH2:45][N:46]2[CH2:51][CH2:50][CH:49]([CH2:52][NH:53][C:54](=[O:60])[C@H:55]([CH:57]([CH3:59])[CH3:58])[NH2:56])[CH2:48][CH2:47]2)=[CH:43][CH:42]=1>ClCCl>[Cl:40][C:41]1[CH:62]=[CH:61][C:44]([CH2:45][N:46]2[CH2:47][CH2:48][CH:49]([CH2:52][NH:53][C:54](=[O:60])[C@H:55]([CH:57]([CH3:59])[CH3:58])[NH:56][C:13](=[O:15])[C:12]3[CH:16]=[CH:17][CH:18]=[C:10]([C:8]#[N:9])[CH:11]=3)[CH2:50][CH2:51]2)=[CH:43][CH:42]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 158753-Cyanobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 53782731HCID 53782731, Verbindung

Produkt 1

HCID 54167831HCID 54167831, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Triethylamine (0.011 mL, 0.077 mmol), m-cyanobenzoic acid (28 mg, 0.071 mmol), EDCI (13 mg, 0.065 mmol) and HOBt (9 mg, 0.065 mmol) were added to a dichloromethane (0.60 mL) solution of 1-(4-chlorobenzyl)-4-[(valylamino)methyl]piperidine (20 mg, 0.059 mmol). The resulting reaction mixture was stirred at 25° C. for 16 hours, and the obtained solution was diluted with dichloromethane (0.75 mL), washed with a 2 M aqueous solution of NaOH (0.75 mL×2) and dried by filtration through a PTFE membrane. The dried solution was concentrated to thereby afford 1-(4-chlorobenzyl)-4-[[N-(3-cyanobenzoyl)valyl]aminomethyl]piperidine (Compd. No. 619) (24.2 mg, 88%). Further purification was not required for the resulting compound. The purity was determined by RPLC/MS (85%). ESI/MS m/e 467 (M++H, C26H31ClN4O2).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. washwashed with a 2 M aqueous solution of NaOH (0.75 mL×2)
  3. dry with materialdried by filtration through a PTFE membrane
  4. concentrationThe dried solution was concentrated to thereby afford 1-(4-chlorobenzyl)-4-[[N-(3-cyanobenzoyl)valyl]aminomethyl]piperidine (Compd. No
  5. customFurther purification

Quellen und Nachweise

ORD-Eintrag
ord-9118149ce9c1418c94ac761cef4a7bdc
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390830B1

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