4-(Pyrrolidin-1-ylmethyl)aniline → HCID 178426943, Verbindung

HRID 640973

Reaktionsgleichung

Reaktionsgleichung von HRID 640973
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:30].[N:31]1([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([NH2:43])=[CH:39][CH:38]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1>C1COCC1>[O:30]=[C:4]1[C:3](=[CH:2][NH:43][C:40]2[CH:39]=[CH:38][C:37]([CH2:36][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:42][CH:41]=2)[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5]1

Komponenten

4

Edukt 2

HCID 7768524-(Pyrrolidin-1-ylmethyl)anilineHCID 178426964HCID 178426964, Verbindung

Produkt 1

HCID 178426943HCID 178426943, VerbindungAusbeute 26,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

was charged with 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 60, 100 mg, 0.249 mmol) and THF (2 mL). To the resulting solution was added 4-Pyrrolidin-1-ylmethyl-phenylamine (43.8 mg, 0.249 mmol), and the mixture was stirred for 24 h at 65° C. The reaction mixture was cooled to room temperature. Hexanes were added to the reaction mixture causing a black precipitate to form. The precipitate was vacuum filtered and the filtrate was then concentrated in vacuo and redissolved into ˜3 mL of EtOAc. Hexanes were added causing a yellow precipitate to form. The precipitate was then filtered and washed with ˜1 mL of i-prOH yielding 15% (0.021 g, 0.067 mmol) of the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto form
  3. filtrationfiltered
  4. concentrationthe filtrate was then concentrated in vacuo
  5. dissolutionredissolved into ˜3 mL of EtOAc
  6. additionHexanes were added
  7. customto form
  8. filtrationThe precipitate was then filtered

Quellen und Nachweise

ORD-Eintrag
ord-8e667c20d5f74b05b1718df920803f53
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07692005B2

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