Diisopropylamine → 5-p-Tolylethinylfuran-2-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

HRID 1354712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1354712
C(NC(C)C)(C)C.[CH3:8][N:9]([CH3:30])[CH:10]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[O:25][C:26](Br)=[CH:27][CH:28]=3)=[O:23])=[CH:17][CH:16]=2)[CH2:11]1.[C:31]([C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=1)#[CH:32]>CN(C=O)C>[CH3:8][N:9]([CH3:30])[CH:10]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[O:25][C:26]([C:32]#[C:31][C:33]4[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=4)=[CH:27][CH:28]=3)=[O:23])=[CH:17][CH:16]=2)[CH2:11]1

Komponenten

5

Edukt 3

HCID 7912DiisopropylamineHCID 13018p-EthynyltolueneHCID 671477595-Bromofuran-2-carboxylic Acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

Produkt 1

HCID 588675915-p-Tolylethinylfuran-2-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

0.042 ml of diisopropylamine was added under argon to 3.8 mg of Pd(tBu)2Cl2 and 0.95 mg of Cul in 0.2 ml of DMF. A solution of 94.6 mg of 5-bromofuran-2-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]-amide in 0.3 ml of DMF and a solution of 4-ethynyltoluene in 0.3 ml of DMF were then added dropwise. The solution was stirred at room temperature overnight. The precipitate which had separated out was filtered off with suction and the filtrate purified by preparative HPLC. The desired product with the molecular weight of 413.52; MS (ESI): 414 was obtained as hydrotrifluoroacetate.

Aufarbeitung

  1. customThe precipitate which had separated out
  2. filtrationwas filtered off with suction
  3. customthe filtrate purified by preparative HPLC
  4. customMS (ESI): 414 was obtained as hydrotrifluoroacetate

Quellen und Nachweise

ORD-Eintrag
ord-21ad88f9922247dcb650139dd7538a6b
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223788B2

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