2-(2-Phenyldiazenyl)propanedinitrile → HCID 178508325, compound

HRID 346531Notes

Reaction equation

HRID 346531 reaction equation
C[O-].[Na+].[C:4]1([N:10]=[N:11][CH:12]([C:15]#[N:16])[C:13]#[N:14])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:17][C:18]1[CH:36]=[CH:35][CH:34]=[CH:33][C:19]=1[CH2:20][N:21]1[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[C:23]([C:30]([NH2:32])=[NH:31])=[N:22]1>>[F:17][C:18]1[CH:36]=[CH:35][CH:34]=[CH:33][C:19]=1[CH2:20][N:21]1[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[C:23]([C:30]2[N:32]=[C:13]([NH2:14])[C:12](/[N:11]=[N:10]/[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[C:15]([NH2:16])[N:31]=2)=[N:22]1

Participants

4

Reactant 3

HCID 223472-(2-Phenyldiazenyl)propanedinitrileHCID 10942334Sodium MethoxideHCID 114039861-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide2×

Product 1

HCID 178508325HCID 178508325, compound

Conditions

Temperature
110 °C

Procedure

3.87 g of sodium methanolate and then 12.2 g (71.7 mmol) of phenylazomalononitrile (L. F. Cavalieri, J. F. Tanker, A. Bendich, J. Am. Chem. Soc., 1949, 71, 533) are added to a stirred solution of 21.92 g (71.7 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamidine in N,N-dimethylformamide from Example 6A. The mixture is stirred at 110° C. overnight and allowed to cool. The solid which precipitates is filtered off with suction and washed with ethanol. Drying results in 23 g (73% of theory) of the target compound.

Workup

  1. temperatureto cool
  2. customThe solid which precipitates
  3. filtrationis filtered off with suction
  4. washwashed with ethanol
  5. customDrying
  6. customresults in 23 g (73% of theory) of the target compound

Sources & evidence

ORD record
ord-55d0e834d6fb4be8b4ac4733b3551155
Source dataset
uspto-grants-2007_02
Patent number
US07173037B2

Reaction notes

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