Methanol → HCID 86661325, compound

HRID 1685095Notes

Reaction equation

HRID 1685095 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][NH:6][C:7](=[O:27])[NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][N:15]([CH3:26])[C:16]([C:18]2[CH:23]=[C:22]([Cl:24])[N:21]=[N:20][C:19]=2Cl)=[O:17])[N:13]=1.[CH3:31][OH:32].[OH-].[Na+]>O1CCOCC1>[Cl:24][C:22]1[N:21]=[N:20][C:19]([O:32][CH3:31])=[C:18]([C:16]([N:15]([CH2:14][C:12]2[N:13]=[C:9]([NH:8][C:7]([NH:6][CH2:5][C:4]3[CH:28]=[CH:29][CH:30]=[C:2]([F:1])[CH:3]=3)=[O:27])[S:10][CH:11]=2)[CH3:26])=[O:17])[CH:23]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86661318HCID 86661318, compound

Product 1

HCID 86661325HCID 86661325, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3,6-dichloro-pyridazine-4-carboxylic acid {2-[3-(3-fluoro-benzyl)-ureido]-thiazol-4-ylmethyl}-methyl-amide (235 mg, 0.5 mmol) and MeOH (160 mg, 5 mmol) in 1,4-dioxane (10 mL) was added NaOH (20 mg, 0.5 mmol). The mixture was stirred overnight at room temperature and concentrated in vacuo. The residue was dissolved in CH2Cl2+5% MeOH and filtered over a small plug of silica. The volatiles were evaporated and the desired product (230 mg) was obtained as a 5:1 mixture with starting material-3,6-dichloro-pyridazine-4-carboxylic acid {2-[3-(3-fluoro-benzyl)-ureido]-thiazol-4-ylmethyl}-methyl-amide. This mixture was used as such in the subsequent steps.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2+5% MeOH
  3. filtrationfiltered over a small plug of silica
  4. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-6a928b6ec8c24a6a825f306dde45a624
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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