4-Hexylbenzoyl chloride → N-[2-(6-Bromo-2H-pyrazolo[4,3-b]pyridin-2-yl)-1-cyano-1-methylethyl]-4-hexylbenzamide

HRID 1257060Notes

Reaction equation

HRID 1257060 reaction equation
[CH2:1]([C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:16][C:17]([CH3:31])([CH2:20][N:21]1[CH:30]=[C:24]2[N:25]=[CH:26][C:27]([Br:29])=[CH:28][C:23]2=[N:22]1)[C:18]#[N:19]>C1COCC1>[Br:29][C:27]1[CH:26]=[N:25][C:24]2=[CH:30][N:21]([CH2:20][C:17]([NH:16][C:11](=[O:12])[C:10]3[CH:14]=[CH:15][C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:8][CH:9]=3)([C:18]#[N:19])[CH3:31])[N:22]=[C:23]2[CH:28]=1

Participants

4

Reactant 2

HCID 1708634-Hexylbenzoyl chlorideHCID 666201262-Amino-3-(6-bromo-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropionitrile

Product 1

HCID 68708568N-[2-(6-Bromo-2H-pyrazolo[4,3-b]pyridin-2-yl)-1-cyano-1-methylethyl]-4-hexylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using a procedure similar to that described in Example 60, except using a solution of 4-hexylbenzoyl chloride (0.16 mmole) in THF and a solution of 2-amino-3-(6-bromo-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropionitrile (0.075 mmole, described in Example 182) in THF mixed with TEA (3% v./v.), the title compound was isolated as solid residue (13.9 mg). It was dissolved in DMSO for further biological evaluation and analyzed by LCMS. MS (ES): M/Z [M+H]=468, RT=0.76 min.

Sources & evidence

ORD record
ord-ccca8587809e4b40ad1d8a5a264eef70
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

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