Triethylamine → N-(1-benzylpiperidin-4-yl)-N-methyl-1H-indazole-5-carboxamide

HRID 1269776

Reaktionsgleichung

Reaktionsgleichung von HRID 1269776
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([NH:26][CH3:27])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]([CH3:27])[C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)=[O:12])[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

8

Edukt 6

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 41361281-benzyl-N-methylpiperidin-4-amineHCID 42484541H-Indazole-5-carboxylic acidHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 22933863N-(1-benzylpiperidin-4-yl)-N-methyl-1H-indazole-5-carboxamideAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the 1H-indazole-5-carboxylic acid (281 mg, 1.73 mmol) obtained in Reference Example 1 in N,N-dimethylformamide (10 ml) were added 1-benzyl-N-methylpiperidin-4-amine (390 mg, 1.91 mmol), triethylamine (0.29 ml, 2.08 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)-carbodiimide monohydrochloride (499 mg, 2.60 mmol) and hydroxybenzotriazole (281 mg, 2.08 mmol), and the resulting mixture was stirred overnight at room temperature. An aqueous sodium hydrogencarbonate solution was added to the reaction solution, followed by extraction with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate→chloroform/methanol) to obtain N-(1-benzylpiperidin-4-yl)-N-methyl-1H-indazole-5-carboxamide (502 mg, 83%).

Aufarbeitung

  1. extractionfollowed by extraction with chloroform
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate→chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-f98bff7e9af44eb890aeb8d2f479d887
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199147B2

Verknüpfte Notizen

Wird geladen…