HCID 136119122, compound → HCID 57127988, compound

HRID 1421959Notes

Reaction equation

HRID 1421959 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:6]([C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18](=[O:23])[C:17]([OH:24])=[C:16]3[OH:25])[N:12]=1)=[O:7].B.[Na]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]([C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[NH:19][C:18](=[O:23])[C:17]([OH:24])=[C:16]4[OH:25])[N:12]=2)[OH:7])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]

Participants

4

Reactant 2

HCID 136119122HCID 136119122, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 57127988HCID 57127988, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 6 ml of chloroform was dissolved 100 mg of 2-(3,4-dimethoxybenzoyl)-4-(3,4-dihydroxycarbostyril-6-yl)thiazole. Thereto was added sodium boron hydride at room temperature, and the mixture was stirred for 1 hour at the same temperature. The solvent was distilled off. The residue was extracted with chloroform. The extract was water-washed, dried and then subjected to solvent removal by distillation. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=99/1) and then recrystallized from ethyl acetate to obtain 52 mg of 2-[1-(3,4-dimethoxyphenyl)-1-hydroxymethyl]-4-(3,4-dihydroxycarbostyril-6-yl)thiazole as light brown prismatic crystals.

Workup

  1. distillationThe solvent was distilled off
  2. extractionThe residue was extracted with chloroform
  3. washwashed
  4. customdried
  5. customsubjected to solvent removal by distillation
  6. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=99/1)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-504613d7d4694187a3787c79b7bfd729
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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