1-(Methylamino)adamantane → 5-Benzyl-1,3-dimethyl-1h-pyrazole-4-carboxylic acid (adamantan-1-ylmethyl)-amide

HRID 2279643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2279643
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2C=CC=CC=2N=N1.[CH2:28]([C:35]1[N:39]([CH3:40])[N:38]=[C:37]([CH3:41])[C:36]=1[C:42]([OH:44])=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:45]12(NC)[CH2:54][CH:49]3[CH2:50][CH:51]([CH2:53][CH:47]([CH2:48]3)[CH2:46]1)[CH2:52]2.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:45]12([CH2:12][NH:8][C:42]([C:36]3[C:37]([CH3:41])=[N:38][N:39]([CH3:40])[C:35]=3[CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:44])[CH2:46][CH:47]3[CH2:48][CH:49]([CH2:50][CH:51]([CH2:53]3)[CH2:52]1)[CH2:54]2

Komponenten

8

Edukt 5

HCID 194761-(Methylamino)adamantaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 595799845-Benzyl-1,3-dimethyl-1H-pyrazole-4-carboxylic acid

Produkt 1

HCID 595798435-Benzyl-1,3-dimethyl-1h-pyrazole-4-carboxylic acid (adamantan-1-ylmethyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

BOP (44 mg, 0.1 mmol) is added to a solution of 5-benzyl-1,3-dimethyl-1H pyrazole-4-carboxylic acid (20 mg, 0.087 mmol), admantan-1-yl-methylamine (15 mg, 0.09 mmol), HOBt (5 mg) and DIEA (17 μL, 0.1 mmol) in DMF (0.5 mL) at it. The mixture is stirred for 14 h. H2O is added, and the mixture is extracted with EtOAc (3×10 mL). The organic phase is dried. The title compound is obtained by PTLC using 20% EtOAc in hexane. 1H NMR (CDCl3): 7.29-7.21 (m, 3H), 7.12-7.11 (in, 2H), 5.39 (m, 1H), 4.33 (s, 2H), 3.65 (s, 3H), 3.07 (m, 2H), 2.46 (s, 3H), 1.94 (m, 3H), 1.70-1.56 (m, 12H). MS (M+1)=378.22; RT=1.67 min. *IC50.

Aufarbeitung

  1. extractionthe mixture is extracted with EtOAc (3×10 mL)
  2. customThe organic phase is dried

Quellen und Nachweise

ORD-Eintrag
ord-5454bb327f74433781030c2e83611519
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133204B2

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