1H-Indazol-5-amine → Rho-Kinase-IN-3

HRID 734659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734659
[CH3:1][C:2]1[NH:3][C:4](=[O:21])[CH2:5][CH:6]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[C:7]=1[C:8](O)=[O:9].[NH:22]1[C:30]2[C:25](=[CH:26][C:27]([NH2:31])=[CH:28][CH:29]=2)[CH:24]=[N:23]1>CN(C=O)C>[NH:22]1[C:30]2[C:25](=[CH:26][C:27]([NH:31][C:8]([C:7]3[CH:6]([C:11]4[CH:20]=[CH:19][C:18]5[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=5)[CH:12]=4)[CH2:5][C:4](=[O:21])[NH:3][C:2]=3[CH3:1])=[O:9])=[CH:28][CH:29]=2)[CH:24]=[N:23]1

Komponenten

4

Edukt 2

HCID 880121H-Indazol-5-amineHCID 160998652-Methyl-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

Produkt 1

HCID 11269477Rho-Kinase-IN-3Ausbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The product of step 2 (450 mg, 1.60 mmol, 1 equiv) was combined with 1H-indazol-5-amine (212 mg, 1.60 mmol, 1 equiv) and polystyrene-bound carbodiimide (1.78 g, 1.1 mmol/g, 1.97 mmol, 1.2 equiv) in 6 mL DMF. The reaction mixture was stirred for 22 hours at room temperature. The resin was removed by filtration and washed alternately with CH2Cl2 and MeOH, ending with CH2Cl2. The volatile solvents were removed en vacuo and water was added, providing a solid residue. The residue was triturated with ethyl acetate, affording 140 mg of the title compound as a white crystalline solid. MS (ES+) m/e 397 [M+H]+

Aufarbeitung

  1. customThe resin was removed by filtration
  2. washwashed alternately with CH2Cl2 and MeOH
  3. customThe volatile solvents were removed en vacuo and water
  4. additionwas added
  5. customproviding a solid residue
  6. customThe residue was triturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5716b9cbeb704cdc87f8e54ddf2adac0
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592357B2

Notizen zur Reaktion

Wird geladen…