1-Isocyanato-2-phenoxybenzene → 5-(2-hydroxyphenyl)-N-(2-phenoxyphenyl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazole-1-carboxamide

HRID 1712958

Reaktionsgleichung

Reaktionsgleichung von HRID 1712958
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[C:2]=[O:3].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH2:27][CH:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[OH:34])[NH:25][N:24]=2)[CH:18]=1>CN(C=O)C.ClCCCl.C(=O)(O)[O-].[Na+]>[OH:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH:26]1[N:25]([C:2]([NH:1][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:3])[N:24]=[C:23]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)[CH2:27]1

Komponenten

6

Edukt 2

HCID 27333891-Isocyanato-2-phenoxybenzeneHCID 226963962-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol

Produkt 1

HCID 249643015-(2-hydroxyphenyl)-N-(2-phenoxyphenyl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazole-1-carboxamideAusbeute 12,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of 1-isocyanato-2-phenoxybenzene (29.14 mg, 0.138 mmol) in DMF (0.5 mL) was added a solution of 2-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol (29.9 mg, 0.125 mmol) in DMF (0.5 mL) and DCE (0.5 mL) at rt. The reaction mixture was shaken at rt for 20 h. The reaction mixture was diluted with a saturated solution of sodium bicarbonate (2 mL) and extracted with DCM. The organic solutions were combined, dried over MgSO4, filtered, and concentrated. The residue was purified by RP-HPLC to give 5-(2-hydroxyphenyl)-N-(2-phenoxyphenyl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazole-1-carboxamide (I-85) (7.24 mg, 12.8%). LCMS: (FA) ES+ 451.3.

Aufarbeitung

  1. extractionextracted with DCM
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ee5ea791f15e488aae2a131de2fff87c
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795249B2

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