Potassium Hydroxide → HCID 197504, compound

HRID 1590704Notes

Reaction equation

HRID 1590704 reaction equation
[OH-].[K+].Cl.[CH2:4]([N:6]([CH2:34][CH3:35])[CH2:7][CH:8]([OH:33])[CH2:9][NH:10][C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[C:14]([NH:27][CH2:28][CH:29]([OH:32])[CH2:30]Cl)=[CH:13][CH:12]=1)[CH3:5]>CO>[CH2:4]([N:6]([CH2:34][CH3:35])[CH2:7][CH:8]([OH:33])[CH2:9][NH:10][C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[C:14]([NH:27][CH2:28][CH:29]2[O:32][CH2:30]2)=[CH:13][CH:12]=1)[CH3:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 368387HCID 368387, compound2×

Product 1

HCID 197504HCID 197504, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (0.3 g, 5.36 mmole) was added to a solution of 1-(3-diethylamino-2-hydroxypropylamino)-4-(3-chloro-2-hydroxypropylamino)-9, 10-anthracenedione hydrochloride salt (1 g, 1.78 mmole), the compound of Example 3, in methanol. The mixture was stirred at room temperature for 48 hours. Solvent was removed under reduced pressure and the residue was purified by flash column chromatography (silica gel, chloroform with a methanol gradient up to a ratio of 10:1) to give the title product 1-(3-diethylamino-2-hydroxypropylamino)-4-(2, 3-epoxypropylamino)-9, 10-anthracenedione which is compound 1b-1 of Table 1 (391 mg, 52%), mp 98° C.: NMR (CDCl3) δ 1.06 (t, J=7.1 Hz, 6H, CH3), 2.62 (m, 7H, CH2), 2.87 (m, 1H, CH2), 3.27 (m, 1H, CH2), 3.49 (m, 2H, CH2), 3.59 (m, 1H CH2), 3.77 (m, 1H, CH), 3.96 (m, 1H, CH), 7.35 (s, 2H, Ar (2, 3)), 7.71 (m, 2H, Ar (6, 7)), 8.35 (m, 2H, Ar (5, 8)), 10.80 (b, 1H, NH), 10.92 (b, 1H, NH); Anal. Calcd for C24H29N3O4 : C, 68.1; H, 6.90; N, 9.92. Found: C, 67.86; H, 6.96; N, 9.85.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue was purified by flash column chromatography (silica gel, chloroform with a methanol

Sources & evidence

ORD record
ord-1f99c6cb083b40dd95d8b498a1b5531e
Source dataset
uspto-grants-1993_04
Patent number
US05204370

Reaction notes

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