Dimethylformamide → 2-{3-Pyridin-3-yl-1-[(5-pyridin-2-yl-2-thienyl)carbonyl]-4,5-dihydro-1h-pyrazol-5-yl}phenol

HRID 1712956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1712956
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[NH:9][N:8]=2)[CH:2]=1.N1C=CC=CC=1[C:25]1[CH:29]=[CH:28][S:27][C:26]=1[C:30](O)=[O:31].CCN=C=N[CH2:38][CH2:39][CH2:40][N:41]([CH3:43])C.[CH3:44]N(C=O)C>C(Cl)Cl.CCOC(C)=O.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[N:9]([C:30]([C:26]3[S:27][C:28]([C:40]4[CH:39]=[CH:38][CH:44]=[CH:43][N:41]=4)=[CH:29][CH:25]=3)=[O:31])[N:8]=2)[CH:2]=1

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 102420433-(Pyridin-2-yl)thiophene-2-carboxylic acidHCID 226963962-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol

Produkt 1

HCID 249635882-{3-Pyridin-3-yl-1-[(5-pyridin-2-yl-2-thienyl)carbonyl]-4,5-dihydro-1h-pyrazol-5-yl}phenolAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol (600 mg, 2.51 mmol) and pyridine-2-ylthiophene-2-carboxylic acid (515 mg, 2.51 mmol) in DCM (10 mL) was added EDCI (580 mg, 3.00 mmol) and DMF (3 mL). After stirring for 12 h, water and EtOAc were added. The resulting solid was filtered and washed with EtOAc and cold MeOH and dried under vacuum to give 2-[3-pyridin-3-yl-1-[(5-pyridin-2-yl-2-thienyl)carbonyl]-4,5-dihydro-1H-pyrazol-5-yl]phenol (I-76) (520 mg, 49%). LCMS: (AA) ES+ 427.4.

Aufarbeitung

  1. filtrationThe resulting solid was filtered
  2. washwashed with EtOAc and cold MeOH
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8f7cf0907c69431991e4513c4b93f966
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795249B2

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