Triethylamine → HCID 25122028, Verbindung

HRID 37877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 37877
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.C(N(CC)CC)C.[O:26]=[C:27]([C:31]1[N:39]2[C:34]([CH2:35][CH2:36][CH2:37][CH2:38]2)=[CH:33][C:32]=1[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:28](Cl)=[O:29]>C(Cl)Cl>[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:28](=[O:29])[C:27](=[O:26])[C:31]3[N:39]4[C:34]([CH2:35][CH2:36][CH2:37][CH2:38]4)=[CH:33][C:32]=3[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 242791974-[4-(2,2-Dimethyl-propyl)-piperazin-1-yl-]-phenylamineHCID 86649692Oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride

Produkt 1

HCID 25122028HCID 25122028, VerbindungAusbeute 36,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To an ice-cold solution of 4-[4-(2,2-dimethyl-propyl)-piperazin-1-yl]-phenylamine (prepared as described in Reference Example 93, 300 mg, 1.21 mmol) and triethylamine (0.33 mL, 2.4 mmol) in dry DCM (12 mL) was added a solution of oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride (prepared as described in Reference Example 21, 407 mg, 1.41 mmol) in DCM (5 mL). The mixture was warmed to room temperature and stirred for 30 min then diluted with DCM, washed successively with water, sodium bicarbonate solution and brine, then dried over sodium sulfate. Concentration gave a residue which was purified by preparative TLC using ethyl acetate and hexane (3:7) as eluent to afford N-{4-[4-(2,2-dimethyl-propyl)-piperazin-1-yl]-phenyl}-2-oxo-2-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetamide (220 mg, 36%) as a yellow powder.

Aufarbeitung

  1. washwashed successively with water, sodium bicarbonate solution and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration
  4. customgave a residue which
  5. customwas purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-27038262d7744d498bc2c42bceb5bb6d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524705B2

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