(2Z)-3-Amino-2-butenenitrile → HCID 135844963, compound

HRID 1951548Notes

Reaction equation

HRID 1951548 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])=O.[CH3:13][C:14]1[N:15]=[C:16]([CH2:19][C:20](=O)[CH2:21][CH2:22][CH3:23])[S:17][CH:18]=1.[NH2:25]/[C:26](/[CH3:30])=[CH:27]\[C:28]#[N:29]>C(O)(C)C>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]2[C:19]([C:16]3[S:17][CH:18]=[C:14]([CH3:13])[N:15]=3)=[C:20]([CH2:21][CH2:22][CH3:23])[NH:25][C:26]([CH3:30])=[C:27]2[C:28]#[N:29])=[C:4]([O:11][CH3:12])[CH:5]=1)#[N:8]

Participants

5

Reactant 3

HCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 166592514-Formyl-3-methoxybenzonitrileHCID 59492362HCID 59492362, compound

Product 1

HCID 135844963HCID 135844963, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

100 mg (0.620 mmol) of the compound from example 3A, 114 mg (0.620 mmol) of the compound from example 12A and 51 mg (0.620 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). 134 mg (66% 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-c9931b9371c742aaa4ef1e3e0d58f343
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

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