Midaxifylline → HCID 14686248, compound

HRID 1768743Notes

Reaction equation

HRID 1768743 reaction equation
NC1(C2N[C:14]3[C:13](=[O:16])[N:12]([CH2:17][CH2:18]C)C(=O)N(CCC)[C:9]=3[N:8]=2)CCCC1.C(C(C(Cl)=O)C(Cl)=[O:28])C>O1CCCC1.N1C=CC=CC=1>[CH2:17]([NH:12][C:13](=[O:16])[CH2:14][C:9]([NH2:8])=[O:28])[CH3:18]

Participants

5

Reactant 2

HCID 3047747MidaxifyllineHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 14686248HCID 14686248, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of 4.5 g di 8-(1-aminocyclopentyl)-1,3-dipropylxanthine in 45 ml of anhydrous tetrahydrofurane, 1.4 ml of pyridine are added and, after cooling to 5° C., 2.26 ml of ethyl malonyl chloride are dropwise added. The mixture is stirred at room temperature for 2 hours, followed by concentration under vacuum, addition of 1N HCl and extraction with ethyl acetate. The organic phase is washed with water, dried and evaporated, thereby obtaining 6.5 g of raw product which is purified by column chromatography (SiO2). 2.6 g of mono malonamide mono ethyl ester are obtained, which is finally saponified by treatment with tetrahydrofurane (26 ml) and NaOH 1N (30 ml) at room temperature for 1 hour.

Workup

  1. additionare added
  2. concentrationfollowed by concentration under vacuum, addition of 1N HCl and extraction with ethyl acetate
  3. washThe organic phase is washed with water
  4. customdried
  5. customevaporated
  6. customobtaining 6.5 g of raw product which
  7. customis purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-e8683ce432494d90b40c79b1c713a941
Source dataset
uspto-grants-1995_01
Patent number
US05378844

Reaction notes

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