Butyl iodide → 1-Butyl-6-chloro-4-methyl-3-oxo-1,3-dihydropyrazolo[3,4-b]pyridine-2-carboxylic acid (2-thiophen-2-ylethyl)amide

HRID 1685231Notes

Reaction equation

HRID 1685231 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][NH:8][C:9]([N:11]1[C:19](=[O:20])[C:18]2[C:13](=[N:14][C:15]([Cl:22])=[CH:16][C:17]=2[CH3:21])[NH:12]1)=[O:10].I[CH2:24][CH2:25][CH2:26][CH3:27].[H-].[Na+]>CN(C=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][NH:8][C:9]([N:11]1[C:19](=[O:20])[C:18]2[C:13](=[N:14][C:15]([Cl:22])=[CH:16][C:17]=2[CH3:21])[N:12]1[CH2:24][CH2:25][CH2:26][CH3:27])=[O:10]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 86628145HCID 86628145, compound

Product 1

HCID 866281511-Butyl-6-chloro-4-methyl-3-oxo-1,3-dihydropyrazolo[3,4-b]pyridine-2-carboxylic acid (2-thiophen-2-ylethyl)amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 2, 50 mg (0.148 mmol) of 6-chloro-4-methyl-3-oxo-1,3-dihydropyrazolo[3,4-b]pyridine-2-carboxylic acid (2-thiophen-2-ylethyl)amide were reacted with 41 mg (0.22 mmol) of 1-iodobutane in DMF with sodium hydride. Yield: 8 mg (14%), M+H+: 393.47

Sources & evidence

ORD record
ord-50173ed7deb74b4eb20aab6bf15f2e8d
Source dataset
uspto-grants-2012_04
Patent number
US08148395B2

Reaction notes

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