1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-Ethynyl-N-{2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-benzamide

HRID 1177941

Reaktionsgleichung

Reaktionsgleichung von HRID 1177941
CCN(C(C)C)C(C)C.[C:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)#[CH:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:42][CH2:43][C:44]([N:46]1[CH2:51][CH2:50][N:49]([C:52](=[O:64])[C:53]2[CH:58]=[C:57]([F:59])[CH:56]=[CH:55][C:54]=2[C:60]([F:63])([F:62])[F:61])[CH2:48][CH2:47]1)=[O:45]>CN(C=O)C.O>[C:10]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([NH:42][CH2:43][C:44]([N:46]2[CH2:47][CH2:48][N:49]([C:52](=[O:64])[C:53]3[CH:58]=[C:57]([F:59])[CH:56]=[CH:55][C:54]=3[C:60]([F:62])([F:61])[F:63])[CH2:50][CH2:51]2)=[O:45])=[O:18])=[CH:19][CH:20]=1)#[CH:11]

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5897064-Ethynylbenzoic acidHCID 595595982-Amino-1-[4-(2-trifluoromethyl-5-fluoro-benzoyl)-piperazin-1-yl]-ethanone

Produkt 1

HCID 595595974-Ethynyl-N-{2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-benzamideAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (263.67 mg, 0.34 mL, 2.04 mmol) was added to a stirred solution of 4-Ethynyl-benzoic acid (100 mg, 0.68 mmol) in DMF (1.5 mL). HOBT (92 mg, 0.68 mmol) and EDCI (156.42 mg, 0.81 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone (253 mg, 0.68 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with 5% sodium bicarbonate solution followed by brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was recrystallized from a mixture of EtOAc and ether to afford 130 mg (41.1% yield) of 4-Ethynyl-N-{2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-benzamide. LCMS Purity: 87.29%. 1H NMR (DMSO-d6): δ 8.7 (m, 1H), 8.0-7.8 (m, 3H), 7.6-7.4 (m, 4H), 4.4 (s, 1H), 4.2-4.1 (m, 2H), 3.8-3.4 (m, 3H), 3.2-3.0 (m, 2H).

Aufarbeitung

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with 5% sodium bicarbonate solution
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. customThe obtained residue was recrystallized from a mixture of EtOAc and ether

Quellen und Nachweise

ORD-Eintrag
ord-afd866c37f594f5b806299fae29cb8cd
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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