HCID 13755513, compound → Ammonium Hydroxide

HRID 344637Notes

Reaction equation

HRID 344637 reaction equation
[NH2:1]CCNC(COC1C=CC([C:15]2[CH:16]([CH3:22])[CH2:17][C:18](=[O:21])[NH:19][N:20]=2)=CC=1)=[O:6].O1CCN(C2C=CC=CC=2OC[C@H]2OC2)CC1>CO>[NH4+:1].[OH-:6].[CH3:22][CH:16]1[CH:15]=[N:20][NH:19][C:18](=[O:21])[CH2:17]1

Participants

5

Reactant 2

HCID 13755513HCID 13755513, compoundHCID 15016312HCID 15016312, compound

Product 2

HCID 14923Ammonium HydroxideHCID 21479294HCID 21479294, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 304 mg (1.00 mmol) of 6-[4-[2-aminoethylcarbamoylmethoxy]phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone, prepared as in Example 1, and 176 mg (0.75 mmol) of (2S)-3-(2-morpholinophenoxy)-1,2-epoxypropane in 5 ml of CH3OH is heated at reflux under N2 for 5 hrs. The solvent was removed under vacuum and the residue flash chromatographed on silica gel using 250 ml of 95:5 CHCl3 :CH3OH, then 250 ml of 90:10:1 CHCl3 :CH3OH:NH4OH and finally 250 ml of 90:10:2 CHCl3 :CH3OH:NH4OH to give 227 mg of 6-{4-[N-[2-morpholinophenyl]-2-hydroxypropylamino]ethyl]carbamoylmethoxyphenyl]}-5-methyl-4,5-dihydro-3(2H)pyridazinone as a white solid. Yield, 56%. This material is taken up in 20 ml of EtOAc and the maleate salt precipitated by the addition of 0.10 M maleic acid in ethyl ether. After drying overnight under high vacuum at 50° C., 243 mg of the maleate salt is obtained as a white powder, m.p. 62° (d).

Workup

  1. temperatureis heated
  2. temperatureat reflux under N2 for 5 hrs
  3. customThe solvent was removed under vacuum
  4. customthe residue flash chromatographed on silica gel using 250 ml of 95:5 CHCl3

Sources & evidence

ORD record
ord-0af92645d97a414c81d2aba4bf1b60cb
Source dataset
uspto-grants-1991_10
Patent number
US05053338

Reaction notes

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