Sodium Cyanide → 2-Ethyl-9-methyl-10-oxo-13-[2-(pyridin-4-yl)ethyl]-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carbonitrile

HRID 724925Notes

Reaction equation

HRID 724925 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:28])[C:7](=[O:27])[C:8]3[CH:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.[C-:29]#[N:30].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:29]([C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:28])[C:7](=[O:27])[C:8]3[CH:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1)#[N:30]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 4706665-Chloro-2-ethyl-9-methyl-13-[2-(pyridin-4-yl)ethyl]-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

Product 1

HCID 4707472-Ethyl-9-methyl-10-oxo-13-[2-(pyridin-4-yl)ethyl]-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carbonitrileYield 15%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 2-chloro-5,11-dihydro-11-ethyl-8-[2-(4-pyridyl)ethyl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (78 mg, 0.2 mmol), Sodium cyanide impregnated alumina (2 g/4 g, 0.44 g, 4.5 mmol), and tetrakis(triphenylphosphine)palladium(0) (45 mg, 0.04 mmol) in 5 mL of toluene was heated at 100° C. under argon for 8 hours. The reaction mixture was filtered, and the collected solid was washed with ethyl acetate. The filtrate was concentrated to give a yellow oil, which was purified by flash chromatography (elution with isopropannol-hexanes) and recrystallization (ethyl acetate-hexanes) to afford 11.5 mg (15%) of the title compound, m.p. 149°-150° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe collected solid was washed with ethyl acetate
  3. concentrationThe filtrate was concentrated
  4. customto give a yellow oil, which
  5. customwas purified by flash chromatography (elution with isopropannol-hexanes) and recrystallization (ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-f14bc2b1954648069ea289b2eaad07eb
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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