Water → HCID 9928346, compound

HRID 1246969Notes

Reaction equation

HRID 1246969 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:18]=[CH:17][C:13]3[O:14][CH2:15][O:16][C:12]=3[CH:11]=2)[C:5]([C:19]#[N:20])=[C:4](SC2C=CC=CC=2)[N:3]=1.C([CH:30]([C:34](N)=[O:35])C(N)=O)C.[CH3:37][C:38](C)([O-:40])C.[K+].O>CN(C=O)C>[CH2:38]([O:40][C:34](=[O:35])[CH2:30][C:4]1[C:5]([C:19]#[N:20])=[C:6]([C:10]2[CH:18]=[CH:17][C:13]3[O:14][CH2:15][O:16][C:12]=3[CH:11]=2)[C:7]([C:8]#[N:9])=[C:2]([NH2:1])[N:3]=1)[CH3:37]

Participants

6

Reactant 4

HCID 962WaterHCID 2630232-ethylpropanediamideHCID 11245724HCID 11245724, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 9928346HCID 9928346, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Amino-4-(1,3-benzodioxol-5-yl)-6-(phenylsulfanyl)-3,5-dicyanopyridine (5.00 g, 13.43 mmol) [preparation analogously to J. M. Quintela, J. L. Soto, Anales de Quimica 79, 368–372 (1983)] is initially charged with ethyl malonamide (4.23 g, 23.22 mmol) in absolute DMF (30 ml) under an atmosphere of argon. Potassium tert-butoxide (3.01 g, 26.85 mmol) is added, and the solution is then stirred at room temperature for 22 hours. The mixture is poured into water (300 ml). The mixture is then extracted three times with ethyl acetate (300 ml each) and the combined organic phases are dried over magnesium sulfate, filtered and concentrated to about 100 ml. The precipitated crystals are filtered off with suction.

Workup

  1. extractionThe mixture is then extracted three times with ethyl acetate (300 ml each)
  2. dry with materialthe combined organic phases are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to about 100 ml
  5. filtrationThe precipitated crystals are filtered off with suction

Sources & evidence

ORD record
ord-3358086eb5d543968b9a9722a51cbf6c
Source dataset
uspto-grants-2006_10
Patent number
US07129255B2

Reaction notes

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