(2Z)-3-Amino-2-butenenitrile → HCID 135844979, compound

HRID 1951560Notes

Reaction equation

HRID 1951560 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=O)=[CH:4][CH:3]=1.[CH3:14][C:15]1[N:16]=[C:17]([CH2:20][C:21]([CH3:23])=O)[S:18][CH:19]=1.[NH2:24]/[C:25](/[CH3:29])=[CH:26]\[C:27]#[N:28]>C(O)(C)C>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]2[C:20]([C:17]3[S:18][CH:19]=[C:15]([CH3:14])[N:16]=3)=[C:21]([CH3:23])[NH:24][C:25]([CH3:29])=[C:26]2[C:27]#[N:28])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 70225244-Fluoronaphthalene-1-carbaldehydeHCID 179309881-(4-Methyl-1,3-thiazol-2-yl)propan-2-one

Product 1

HCID 135844979HCID 135844979, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

150 mg (0.861 mmol) of 4-fluoro-1-naphthaldehyde, 134 mg (0.861 mmol) of the compound from example 4A and 70 mg (0.861 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 purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 14 mg (4% of theory) of the title compound are obtained.

Workup

  1. customthe volatile components are removed in a rotary evaporator
  2. customthe crude product is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)

Sources & evidence

ORD record
ord-07d889e4a96c4e7cb0c7b50d9e219b2e
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

Loading…