2-Hydrazinylpyridine-4-carbonitrile → HCID 68704935, compound

HRID 1913173Notes

Reaction equation

HRID 1913173 reaction equation
[NH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][N:10]=1)[C:6]#[N:7])[NH2:2].CN(C)[CH:13]=[C:14]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[C:15](OCC)=[O:16]>C(O)(=O)C>[C:6]([C:5]1[CH:8]=[CH:9][N:10]=[C:3]([N:1]2[C:15](=[O:16])[C:14]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:13][NH:2]2)[CH:4]=1)#[N:7]

Participants

4

Reactant 2

HCID 201187142-Hydrazinylpyridine-4-carbonitrileHCID 687048643-(Dimethylamino)-2-pyridin-3-yl-acrylic acid ethyl ester

Product 1

HCID 68704935HCID 68704935, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

545 mg (4.06 mmol) of the compound from Example 1A and 1.07 g (4.88 mmol) of the compound from Example 2A in 15 ml of glacial acetic acid are stirred at RT for 2 h. The mixture is concentrated and the residue is taken up in 300 ml of ethyl acetate and washed repeatedly with saturated sodium bicarbonate solution. The organic phase is dried over sodium sulfate, filtered and concentrated. The residue is taken up in 30 ml of ethanol, 1.33 g (4.88 mmol) of a 25% strength solution of sodium ethoxide in ethanol are added at RT and the mixture is stirred for 30 min. The pH is adjusted to 5 by addition of 1 M hydrochloric acid, and the solid formed is filtered off with suction, washed with diethyl ether and dried under high vacuum.

Workup

  1. concentrationThe mixture is concentrated
  2. washwashed repeatedly with saturated sodium bicarbonate solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. addition1.33 g (4.88 mmol) of a 25% strength solution of sodium ethoxide in ethanol are added at RT
  7. additionThe pH is adjusted to 5 by addition of 1 M hydrochloric acid
  8. customthe solid formed
  9. filtrationis filtered off with suction
  10. washwashed with diethyl ether
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-681170ff168b44409240ab3869809240
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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