2-(Ethoxymethylene)propanedinitrile → HCID 89648919, compound

HRID 1774534Notes

Reaction equation

HRID 1774534 reaction equation
C[O-].[Na+].Cl.[CH:5]1([C:8]2[N:12]([CH2:13][C:14]3[C:19]([F:20])=[CH:18][C:17]([O:21][CH2:22][CH3:23])=[CH:16][C:15]=3[F:24])[N:11]=[C:10]([C:25](=[NH:27])[NH2:26])[C:9]=2[CH3:28])[CH2:7][CH2:6]1.C(O[CH:32]=[C:33]([C:36]#[N:37])[C:34]#[N:35])C>>[NH2:37][C:36]1[C:33]([C:34]#[N:35])=[CH:32][N:26]=[C:25]([C:10]2[C:9]([CH3:28])=[C:8]([CH:5]3[CH2:7][CH2:6]3)[N:12]([CH2:13][C:14]3[C:19]([F:20])=[CH:18][C:17]([O:21][CH2:22][CH3:23])=[CH:16][C:15]=3[F:24])[N:11]=2)[N:27]=1

Participants

4

Reactant 3

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 10942334Sodium MethoxideHCID 89648384HCID 89648384, compound

Product 1

HCID 89648919HCID 89648919, compound

Conditions

Temperature
65 °C

Procedure

146 mg of sodium methanolate (2.70 mmol, 1.0 eq) were diluted in 20 ml of methanole at room temperature under a nitrogen atmosphere. Then 1.0 g of 5-cyclopropyl-1-(4-ethoxy-2,6-difluorobenzyl)-4-methyl-1H-pyrazole-3-carboximidamide hydrochloride 1:1 1-3-6 (2.70 mmol, 1.0 eq) and 329 mg of (ethoxymethylene)malononitrile (2.70 mmol, 1.0 eq) were added and the mixture was stirred at 65° C. bath temperature for 18 hours. After cooling to rt the reaction mixture was concentrated in vacuo and purified via HPLC (ACN/H2O/0.2% NH3) to give 284 mg (0.65 mmol, 24%) of analytically pure target compound.

Workup

  1. temperatureAfter cooling to rt the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompurified via HPLC (ACN/H2O/0.2% NH3)
  4. customto give 284 mg (0.65 mmol, 24%) of analytically pure target compound

Sources & evidence

ORD record
ord-acfe764e917f4f22b6dba03515d3d38d
Source dataset
uspto-grants-2016_02
Patent number
US09260412B2

Reaction notes

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