(2Z)-3-Amino-2-butenenitrile → HCID 67018067, compound

HRID 1951561Notes

Reaction equation

HRID 1951561 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.[CH2:13]([C:15]1[S:19][C:18]([CH2:20][C:21]([CH3:23])=O)=[N:17][CH:16]=1)[CH3:14].[NH2:24]/[C:25](/[CH3:29])=[CH:26]\[C:27]#[N:28]>C(O)(C)C>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]2[C:20]([C:18]3[S:19][C:15]([CH2:13][CH3:14])=[CH:16][N:17]=3)=[C:21]([CH3:23])[NH:24][C:25]([CH3:29])=[C:26]2[C:27]#[N:28])=[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 59492364HCID 59492364, compound

Product 1

HCID 67018067HCID 67018067, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

47.6 mg (0.295 mmol) of the compound from example 3A, 50 mg (0.295 mmol) of the compound from example 24A and 24 mg (0.295 mmol) of 3-aminocrotononitrile are dissolved in 2 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). 23 mg (19% of theory) of the title compound are obtained in 90% purity (by LC-MS) and can be further purified by crystallization from ethyl acetate. 3 mg (3% of theory) of the target compound are thus isolated in pure form.

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-a15661a533d54d6c8837340d48bf9dca
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

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