1-Hydroxybenzotriazole → HCID 178438024, compound

HRID 2360683Notes

Reaction equation

HRID 2360683 reaction equation
[CH2:1]([C:3]1[C:11]2[C:10]([C:12](O)=[O:13])=[CH:9][C:8]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([F:22])[CH:16]=3)=[N:7][C:6]=2[NH:5][N:4]=1)[CH3:2].[N:23]1([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(=O)([O-])O.[Na+]>O1CCCC1.CN(C)C(=O)C>[C:32]([O:31][C:29]([N:23]1[CH2:28][CH2:27][N:26]([C:12]([C:10]2[C:11]3[C:3]([CH2:1][CH3:2])=[N:4][NH:5][C:6]=3[N:7]=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([F:22])[CH:16]=3)[CH:9]=2)=[O:13])[CH2:25][CH2:24]1)=[O:30])([CH3:35])([CH3:33])[CH3:34]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178438025HCID 178438025, compound

Product 1

HCID 178438024HCID 178438024, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

To a suspension of 3-ethyl-6-(3-fluoro-4-hydroxy-phenyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.25 g, 0.83 mmol), tert-butyl piperazine-1-carboxylate (0.17 g, 0.91 mmol), 1-hydroxybenzotriazole (0.11 g, 0.83 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.16 g, 0.83 mmol) in anhydrous tetrahydrofurane (5 ml) was added dry N,N-dimethylacetamide (2 ml). The reaction mixture was stirred at room temperature under nitrogen overnight. A solution of saturated sodium hydrogen carbonate was then added, the resulting precipitate was filtered off to afford the title compound (0.25 g, 66%) as a beige solid.

Workup

  1. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-f583e3d6d5e743d0ad5953119993bbb0
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

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