Amonafide → 618863-54-0

HRID 1611640Notes

Reaction equation

HRID 1611640 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][N:6]1[C:20](=[O:21])[C:15]2=[CH:16][C:17]([NH2:19])=[CH:18][C:13]3[C:14]2=[C:9]([CH:10]=[CH:11][CH:12]=3)[C:7]1=[O:8])[CH3:3].[C:22]([O-:30])(=[O:29])[C@H:23]([CH2:25][C:26]([O-:28])=[O:27])[OH:24]>>[CH3:3][N:2]([CH2:4][CH2:5][N:6]1[C:20](=[O:21])[C:15]2=[CH:16][C:17]([NH2:19])=[CH:18][C:13]3[C:14]2=[C:9]([CH:10]=[CH:11][CH:12]=3)[C:7]1=[O:8])[CH3:1].[CH2:25]([C:26]([OH:28])=[O:27])[C@H:23]([OH:24])[C:22]([OH:30])=[O:29]

Participants

3

Reactant 2

HCID 50515Amonafide2×HCID 5459792HCID 5459792, compound

Product 1

HCID 10216431618863-54-0Yield 93%

Procedure

A batch of amonafide L-malate was prepared in accordance with the method of Example I. The material so obtained was 99.4% chromatographically pure on a 10 gram synthetic scale, consistent with previous findings on the larger scale. The material was then converted to the free base amonafide, as follows: 10 grams of the L-malate salt were dissolved in 100 ml distilled water and titrated with vigorous stirring to pH 7 by the addition of ¼ concentrated ammonium hydroxide. The large mass of yellow needles that formed was filtered by suction, washed with water, and recrystalized from ethanol to afford 5.8 gr. Of 99.8% chromatographically pure amonafide free base, mp 172° C. (MW 283.3, 93% yield).

Workup

  1. customThe material so obtained
  2. distillationdistilled water
  3. customThe large mass of yellow needles that formed
  4. filtrationwas filtered by suction
  5. washwashed with water
  6. customrecrystalized from ethanol
  7. customto afford 5.8 gr

Sources & evidence

ORD record
ord-8057aa7332924be49241ac741f765c25
Source dataset
uspto-grants-2006_01
Patent number
US06989390B2

Reaction notes

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