(2Z)-3-Amino-2-butenenitrile → HCID 135844977, compound

HRID 1951558Notes

Reaction equation

HRID 1951558 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH:9]=O)=[CH:7][CH:6]=[CH:5][N:4]=1.[CH3:11][C:12]1[N:13]=[C:14]([CH2:17][C:18]([CH3:20])=O)[S:15][CH:16]=1.[NH2:21]/[C:22](/[CH3:26])=[CH:23]\[C:24]#[N:25]>C(O)(C)C>[CH3:1][O:2][C:3]1[C:8]([CH:9]2[C:17]([C:14]3[S:15][CH:16]=[C:12]([CH3:11])[N:13]=3)=[C:18]([CH3:20])[NH:21][C:22]([CH3:26])=[C:23]2[C:24]#[N:25])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 125333912-Methoxypyridine-3-carbaldehydeHCID 179309881-(4-Methyl-1,3-thiazol-2-yl)propan-2-one

Product 1

HCID 135844977HCID 135844977, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

150 mg (1.09 mmol) of 2-methoxy-3-pyridinecarboxaldehyde, 170 mg (1.09 mmol) of the compound from example 4A and 90 mg (1.09 mmol) of 3-aminocrotononitrile are dissolved in 4 ml of isopropanol and stirred at the reflux temperature overnight. After cooling to room temperature, the volatile components are removed in a rotary evaporator, and the crude product is taken up in 3 ml of ethyl acetate. The crystallizing solid is removed by filtration. The precipitate obtained in this way is washed with a little diethyl ether. 216 mg (58% of theory) of the title compound are obtained.

Workup

  1. customthe volatile components are removed in a rotary evaporator
  2. customThe crystallizing solid is removed by filtration
  3. customThe precipitate obtained in this way
  4. washis washed with a little diethyl ether

Sources & evidence

ORD record
ord-48b5a14147cd407898da7cfb906ca140
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

Loading…