Potassium Hydroxide → HCID 197504, compound

HRID 2225464Notes

Reaction equation

HRID 2225464 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, compound

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) δ1.06 (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-9d0083d4be774e2a8e8a601563efafa9
Source dataset
uspto-grants-1994_09
Patent number
US05344841

Reaction notes

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