Sodium Cyanide → [3,5-Dichloro-4-(3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b: 4',3'-f]azepin-2-yl)phenyl]acetonitrile

HRID 1043478Notes

Reaction equation

HRID 1043478 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8]Cl)[CH:5]=[C:4]([Cl:10])[C:3]=1[C:11]1[NH:12][C:13]2[C:19]3[CH:20]=[CH:21][N:22]=[CH:23][C:18]=3[NH:17][C:16]3[N:24]=[CH:25][CH:26]=[CH:27][C:15]=3[C:14]=2[N:28]=1.[C-:29]#[N:30].[Na+]>CS(C)=O.CO>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][C:29]#[N:30])[CH:5]=[C:4]([Cl:10])[C:3]=1[C:11]1[NH:12][C:13]2[C:19]3[CH:20]=[CH:21][N:22]=[CH:23][C:18]=3[NH:17][C:16]3[N:24]=[CH:25][CH:26]=[CH:27][C:15]=3[C:14]=2[N:28]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 66887168HCID 66887168, compound

Product 1

HCID 16071908[3,5-Dichloro-4-(3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b: 4',3'-f]azepin-2-yl)phenyl]acetonitrileYield 45.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

A solution of 2-[2,6-dichloro-4-(chloromethyl)phenyl]-3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b:4′,3′-f]azepine (8.7 mg, 0.02 mmol), sodium cyanide (2.0 mg, 0.04 mmol) in dimethyl sulfoxide (1.0 mL) was stirred at 25° C. for 1 hour. The reaction mixture was diluted with methanol and purified on preparative LCMS at pH 10 to give the desired product (3.8 mg, 45%). LC/MS: 419 (M+H)+.

Workup

  1. custompurified on preparative LCMS at pH 10

Sources & evidence

ORD record
ord-71f9ceb1484a4368b186a19ac4bddee7
Source dataset
uspto-grants-2013_10
Patent number
US08563541B2

Reaction notes

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