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

HRID 1257059Notes

Reaction equation

HRID 1257059 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.[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:7]([C:4]3[CH:5]=[CH:6][C:1]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)=[CH:2][CH:3]=3)=[O:8])([C:18]#[N:19])[CH3:31])[N:22]=[C:23]2[CH:28]=1

Participants

4

Reactant 2

HCID 841514-Phenylbenzoyl chlorideHCID 666201262-Amino-3-(6-bromo-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropionitrile

Product 1

HCID 68706866N-[2-(6-Bromo-2H-pyrazolo[4,3-b]pyridin-2-yl)-1-cyano-1-methylethyl]-biphenyl-4-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using a procedure similar to that described in Example 60, except using a solution of biphenyl-4-carbonyl 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 (6.3 mg). It was dissolved in DMSO for further biological evaluation and analyzed by LCMS. MS (ES): M/Z [M+H]=460, RT=0.63 min.

Sources & evidence

ORD record
ord-27b1b4a7ded842dfa1c9a349a8928ed3
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

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