HCID 13755513, compound → Ammonium Hydroxide

HRID 1590781Notes

Reaction equation

HRID 1590781 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 766 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-hydroxpropylamino]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 0.10M 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-22dfb6d86e0d4bd4bc496949ab997f2b
Source dataset
uspto-grants-1993_04
Patent number
US05204463

Reaction notes

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