4-Cyanobenzoyl chloride → HCID 68707662, compound

HRID 1256989Notes

Reaction equation

HRID 1256989 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[NH2:12][C:13]([CH3:29])([CH2:16][N:17]1[N:21]=[C:20]2[C:22]([Br:28])=[CH:23][C:24]([Cl:27])=[C:25]([Br:26])[C:19]2=[N:18]1)[C:14]#[N:15]>C1COCC1>[Cl:27][C:24]1[CH:23]=[C:22]([Br:28])[C:20]2=[N:21][N:17]([CH2:16][C:13]([NH:12][C:7](=[O:8])[C:6]3[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)([C:14]#[N:15])[CH3:29])[N:18]=[C:19]2[C:25]=1[Br:26]

Participants

4

Reactant 2

HCID 801724-Cyanobenzoyl chlorideHCID 666198772-Amino-3-(5-chloro-4,7-dibromo-2H-benzotriazol-2-yl)-2-methylpropionitrile

Product 1

HCID 68707662HCID 68707662, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-cyanobenzoyl chloride (0.16 mmole) in THF was added to a solution of 2-amino-3-(5-chloro-4,7-dibromo-2H-benzotriazol-2-yl)-2-methylpropionitrile (0.075 mmole, described in Example 53) in THF mixed with TEA (3% v./v.). The reaction mixture was stirred 12 hours at room temperature then heated to 45° C. for 6 hours before solvent was evaporated under reduced pressure. The resulting crude product was dissolved in DMSO and purify by semi-preparative HPLC. The desired fractions were collected and evaporated under reduced pressure. The title compound was isolated as solid residue (10.8 mg) that was dissolved in DMSO for further biological evaluation and analyzed by LCMS. MS (ES): M/Z [M+H]=521, RT=0.66 min.

Workup

  1. temperaturethen heated to 45° C. for 6 hours before solvent
  2. customwas evaporated under reduced pressure
  3. dissolutionThe resulting crude product was dissolved in DMSO
  4. custompurify by semi-preparative HPLC
  5. customThe desired fractions were collected
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5425cc7deaac40fca170503bf36650ae
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

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