Methanol → HCID 22105622, compound

HRID 1455957Notes

Reaction equation

HRID 1455957 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH:16]([N:18]([C:21]1[N:26]=[N:25][C:24]([C:27]([O:29]CCCC)=[O:28])=[CH:23][CH:22]=1)[CH2:19][CH3:20])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH:16]([N:18]([C:21]1[N:26]=[N:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][CH:22]=1)[CH2:19][CH3:20])[CH3:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 22105620HCID 22105620, compound

Product 1

HCID 22105622HCID 22105622, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl 6-[N-(1-(2-benzyloxy-5-bromophenyl)-eth-1-yl)-N-ethylamino]pyridazine-3-carboxylate (180mg) was dissolved in THF (5 mL) and methanol (5 mL) and sodium hydroxide solution added (0.61 mL, 2M). The mixture was stirred for one hour at ambient temperature, and then the solvents evaporated off. The resulting foam was dissolved in water (20 mL) and pH adjusted to pH 4-5 with glacial acetic acid. A white precipitate formed which was filtered off, washed with water and dried for 17 hours at 5° C. to give 6-[N-(1-(2-benzyloxy-5-bromophenyl)eth-1-yl)-N-ethylamino]pyridazine-3-carboxylic acid (134 mg, mp 129.2° C.).

Workup

  1. customthe solvents evaporated off
  2. dissolutionThe resulting foam was dissolved in water (20 mL)
  3. customA white precipitate formed which
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried for 17 hours at 5° C.

Sources & evidence

ORD record
ord-b6d6d068c187497ab4bc7c41e14e52ec
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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