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

HRID 1257056Notes

Reaction equation

HRID 1257056 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[NH2:14][C:15]([CH3:29])([CH2:18][N:19]1[CH:28]=[C:22]2[N:23]=[CH:24][C:25]([Br:27])=[CH:26][C:21]2=[N:20]1)[C:16]#[N:17]>C1COCC1>[Br:27][C:25]1[CH:24]=[N:23][C:22]2=[CH:28][N:19]([CH2:18][C:15]([NH:14][C:7](=[O:8])[C:6]3[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=3)([C:16]#[N:17])[CH3:29])[N:20]=[C:21]2[CH:26]=1

Participants

4

Reactant 2

HCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 666201262-Amino-3-(6-bromo-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropionitrile

Product 1

HCID 68705547N-[2-(6-Bromo-2H-pyrazolo[4,3-b]pyridin-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using a procedure similar to that described in Example 60, except using a solution of 4-trifluoromethylbenzoyl 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]=452, RT=0.59 min.

Sources & evidence

ORD record
ord-4d968035a7e442b7a80281ed4ecc1db5
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

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