Methyl iodide → 6-Chloro-1,4-dimethyl-3-oxo-1,3-dihydropyrazolo[3,4-b]pyridine-2-carboxylic acid (S)-indan-1-ylamide

HRID 1685233Notes

Reaction equation

HRID 1685233 reaction equation
[C@@H:1]1([NH:10][C:11]([N:13]2[C:21](=[O:22])[C:20]3[C:15](=[N:16][C:17]([Cl:24])=[CH:18][C:19]=3[CH3:23])[NH:14]2)=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.IC.N1[CH2:28]CCN2CCCCCC=12>CN(C=O)C>[C@@H:1]1([NH:10][C:11]([N:13]2[C:21](=[O:22])[C:20]3[C:15](=[N:16][C:17]([Cl:24])=[CH:18][C:19]=3[CH3:23])[N:14]2[CH3:28])=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86628148HCID 86628148, compound

Product 1

HCID 866281536-Chloro-1,4-dimethyl-3-oxo-1,3-dihydropyrazolo[3,4-b]pyridine-2-carboxylic acid (S)-indan-1-ylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 2, 50 mg (0.146 mmol) of 6-chloro-4-methyl-3-oxo-1,3-dihydropyrazolo[3,4-b]pyridine-2-carboxylic acid (S)-indan-1-ylamide were reacted with 31 mg (0.22 mmol) of iodomethane in DMF with 2,3,4,6,7,8,9,10-octahydro -pyrimido[1,2-a]azepin (DBU). Yield: 6 mg (12%), M+H+: 357.09.

Sources & evidence

ORD record
ord-be13fca550874793b631bb05e457a429
Source dataset
uspto-grants-2012_04
Patent number
US08148395B2

Reaction notes

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