Water → 5-amino-3-(3-ethoxy-4-methoxyphenyl)-1-isopropyl-1H-pyrazole-4-carbonitrile

HRID 731897Notes

Reaction equation

HRID 731897 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:12](OC)=[C:13]([C:16]#[N:17])[C:14]#[N:15])[CH:7]=[CH:8][C:9]=1OC)[CH3:2].Cl.[CH:21]([NH:24][NH2:25])([CH3:23])[CH3:22].[CH2:26](N(CC)CC)C.[OH2:33]>C(O)C>[NH2:15][C:14]1[N:24]([CH:21]([CH3:23])[CH3:22])[N:25]=[C:12]([C:6]2[CH:7]=[CH:8][C:9]([O:33][CH3:26])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)[C:13]=1[C:16]#[N:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 855731-Isopropylhydrazine hydrochlorideHCID 866170192-((3-Ethoxy-4-methoxyphenyl)(methoxy)methylene)malononitrile

Product 1

HCID 687116245-amino-3-(3-ethoxy-4-methoxyphenyl)-1-isopropyl-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-((3-ethoxy-4-methoxyphenyl)(methoxy)methylene)malononitrile (200 mg, 0.78 mmol), isopropylhydrazine hydrogen chloride (86 mg, 0.78 mmol), and triethylamine (0.10 mL, 0.78 mmol) were combined in ethanol (5 mL) and heated to reflux for 90 minutes. The reaction was then cooled to RT, water was added and the aqueous phase was extracted three times with EtOAc. The organic phase was concentrated and carried onto the next step without further characterization. ESI-MS (M+H)+ m/z calcd 301.1, found 301.0

Workup

  1. temperatureheated
  2. temperatureto reflux for 90 minutes
  3. extractionthe aqueous phase was extracted three times with EtOAc
  4. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-710a91357e56473fb409ff3d619309ea
Source dataset
uspto-grants-2009_09
Patent number
US07585868B2

Reaction notes

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