3-Amino-2-butenenitrile → HCID 178488656, compound

HRID 1474454Notes

Reaction equation

HRID 1474454 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=O)[CH:9]=2)[NH:4][N:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=O)[CH2:22][C:23]#[N:24])=[CH:17][CH:16]=1.[NH2:26][C:27]([CH3:31])=[CH:28][C:29]#[N:30]>C(O)CCCC.C(#N)C>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[NH:26][C:27]([CH3:31])=[C:28]([C:29]#[N:30])[CH:11]([C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[NH:4][N:3]=[C:2]4[CH3:1])[C:22]=2[C:23]#[N:24])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 706993-Amino-2-butenenitrileHCID 2333984-MethoxybenzoylacetonitrileHCID 178434286HCID 178434286, compound

Product 1

HCID 178488656HCID 178488656, compound

Reagents, catalysts & solvents 2

HCID 62761-PentanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 250 mg (1.56 mmol) 3-methyl-1H-indazole-5-carbaldehyde (Example 1A), 328 mg (1.88 mmol) 3-(4-methoxyphenyl)-3-oxopropanenitrile and 128 mg (1.56 mmol) 3-aminobut-2-enenitrile in 1-pentanol (1.55 ml) containing powdered 4 Å molecular sieve was heated to 105° C. overnight. After cooling, the reaction mixture was diluted with acetonitrile and directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient) to afford 180 mg (30% of th.) of the racemic title compound.

Workup

  1. additioncontaining
  2. temperatureAfter cooling
  3. customdirectly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient)

Sources & evidence

ORD record
ord-6d3d6e1ada1840adb1ecbea8be981100
Source dataset
uspto-grants-2015_04
Patent number
US09018234B2

Reaction notes

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