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4-tert-Butylbenzaldehyde → HCID 178440762, Verbindung

HRID 493111
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 493111
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[C:15]=2[NH2:21])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:22]([C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>C(O)(C)C.[Pd]>[C:22]([C:26]1[CH:27]=[CH:28][C:29]([C:30]2[NH:20][C:16]3=[N:17][CH:18]=[CH:19][C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[C:15]3[N:21]=2)=[CH:32][CH:33]=1)([CH3:25])([CH3:24])[CH3:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 703244-tert-ButylbenzaldehydeHCID 576808304-(2,3-Diamino-pyridin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 178440762HCID 178440762, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-(2,3-Diamino-pyridin-4-yl)-piperazine-1-carboxylic acid t-butyl ester (6) (368 mg, 1.3 mmol) was dissolved in isopropanol (9 ml) with Pd/C 10% (100 mg) and para-t-butyl benzaldehyde (324 mg, 2 mmol). The mixture was heated to 80° C. for 18 hours. MS showed the disappearance of the diamine starting material. The solvent was filtered through CELITE to remove the palladium, and the solvent was removed under vacuum. The residue was dissolved in NMP (4 ml), TFA (12 ml) was added and the reaction mixture was allowed to stir under nitrogen for 12 hours. MS showed the formation of the title product, and the TFA was removed under vacuum. The crude product-NMP mixture was purified by HPLC Method E to yield the title product 7 (320 mg (74%), 0.96 mmol). 1H NMR (DMSO-d6): δ 13.35 (bs, 1H), 8.75 (bs, 1H), 8.11 (dd, J=7.3 Hz, 2.1 Hz, 2H), 8.01 (d, J=6.2 Hz, 1H), 7.55 (dd, J=7.3 Hz, 2.1 Hz, 2H), 6.60 (d, J=6.2 Hz, 1H), 4.14 (m, 4H), 3.26 (m, 4H), 1.33 (s, 9H). MS (ESI-POS): [M+H]+=336.

Aufarbeitung

  1. filtrationThe solvent was filtered through CELITE
  2. customto remove the palladium
  3. customthe solvent was removed under vacuum
  4. dissolutionThe residue was dissolved in NMP (4 ml)
  5. additionTFA (12 ml) was added
  6. customthe TFA was removed under vacuum
  7. customThe crude product-NMP mixture was purified by HPLC Method E

Quellen und Nachweise

ORD-Eintrag
ord-404c39cdc192416196970c38d3acd066
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07534796B2

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