Dichloromethane → N-(3-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-hydroxyphenyl)-5-methylisoxazole-3-carboxamide

HRID 1685945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685945
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:43][C:44]1[CH:49]=[CH:48][C:47]([OH:50])=[C:46]([C:51]2[N:55]([CH3:56])[N:54]=[CH:53][CH:52]=2)[CH:45]=1.C(Cl)[Cl:58]>>[Cl:58][C:52]1[CH:53]=[N:54][N:55]([CH3:56])[C:51]=1[C:46]1[CH:45]=[C:44]([NH:43][C:7]([C:4]2[CH:3]=[C:2]([CH3:1])[O:6][N:5]=2)=[O:9])[CH:49]=[CH:48][C:47]=1[OH:50]

Komponenten

6

Edukt 5

HCID 6344DichloromethaneHCID 769473-Methyl-5-isoxazolecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1355820244-amino-2-(1-methyl-1H-pyrazol-5-yl)phenol

Produkt 1

HCID 136388020N-(3-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-hydroxyphenyl)-5-methylisoxazole-3-carboxamideAusbeute 59 %

Versuchsvorschrift

To a solution of 5-methylisoxazole-3-carboxylic acid (284.0 mg, 2236.0 μmol) dissolved in DCM(10.0 mL) was added HATU (1020.0 mg, 2683.0 μmol) followed by DIEA (586 μl, 3353 μmol). The solution was stirred at room temperature for 5 minutes. 4-amino-2-(1-methyl-1H-pyrazol-5-yl)phenol (500.00 mg, 2236 μmol) was added and the reaction mixture was stirred at 25° C. for 15 hours. The reaction mixture was subjected to purification by column chromatography (ethyl acetate:hexane 50:50) to afford the title compound as an off-white solid in 59.0% yield. LCMS m/z=333.2 (M+H), 1H NMR (400 MHz, DMSO-d6) δ ppm 2.69 (s, 3 H), 3.66 (s, 3 H), 6.64 (s, 1 H), 7.00 (d, J=8.84 Hz, 1 H), 7.61 (s, 1 H), 7.64 (d, J=2.53 Hz, 1 H), 7.73 (dd, J=8.84, 2.53 Hz, 1 H), 10.04 (s, 1 H), 10.60 (s, 1 H).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at 25° C. for 15 hours
  2. customThe reaction mixture was subjected to purification by column chromatography (ethyl acetate:hexane 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-46542986dbd84d66a1c6ec7c5c465f5d
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148417B2

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