(2Z)-3-Amino-2-butenenitrile → 2,6-Dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-5-(4-methyl-1,3-thiazol-2-yl)-1,4-dihydro-pyridine-3-carbonitrile

HRID 1951547Notes

Reaction equation

HRID 1951547 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=O.[CH3:15][C:16]1[N:17]=[C:18]([CH2:21][C:22]([CH3:24])=O)[S:19][CH:20]=1.[NH2:25]/[C:26](/[CH3:30])=[CH:27]\[C:28]#[N:29]>C(O)(C)C>[CH3:30][C:26]1[NH:25][C:22]([CH3:24])=[C:21]([C:18]2[S:19][CH:20]=[C:16]([CH3:15])[N:17]=2)[CH:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:27]=1[C:28]#[N:29]

Participants

5

Reactant 3

HCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 179309881-(4-Methyl-1,3-thiazol-2-yl)propan-2-one

Product 1

HCID 1358449622,6-Dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-5-(4-methyl-1,3-thiazol-2-yl)-1,4-dihydro-pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

181 mg (0.97 mmol) of the compound from example 11A, 150 mg (0.97 mmol) of the compound from example 4A and 79 mg (0.97 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, the crude material is taken up in 5 ml of ethyl acetate, and the precipitated product is then filtered off 240 mg (64% of theory) of the title compound are obtained.

Workup

  1. customthe volatile components are removed in a rotary evaporator
  2. filtrationthe precipitated product is then filtered off 240 mg (64% of theory) of the title compound
  3. customare obtained

Sources & evidence

ORD record
ord-b932c07c36544c8b8ff9c1a6f9a822af
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

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