Ethanol → HCID 18670596, compound

HRID 1059399Notes

Reaction equation

HRID 1059399 reaction equation
COC[N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[C:16]3[CH:20]=[O:21])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:22]=[CH:23][CH:24]=[N:25][C:5]1=2.C([OH:28])C.[OH-].[Na+]>O1CCCC1.[N+]([O-])([O-])=O.[Ag+]>[N:25]1[C:5]2[NH:4][C:9]3[CH:10]=[C:11]([CH2:14][N:15]4[CH:19]=[CH:18][N:17]=[C:16]4[C:20]([OH:28])=[O:21])[CH:12]=[CH:13][C:8]=3[S:7][C:6]=2[N:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 18670248HCID 18670248, compound

Product 1

HCID 18670596HCID 18670596, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 177 mg of 1-(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)imidazol-2-carbaldehyde in a mixture of tetrahydrofuran (10 ml) with ethanol (10 ml) were added 0.5 ml of an aqueous solution of 0.24 g of silver nitrate and 1.5 N sodium hydroxide (4 ml) and the resulting mixture was stirred at room temperature for 15 hours. After filtering off the insoluble matters, the solution was concentrated under reduced pressure and the crystals of 1-(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)imidazol-2-carboxylic acid thus precipitated were taken up by filtration. Next, the crystals were treated by the same method as the one of Example 9 to thereby give 55 mg of the title compound as orange crystals.

Workup

  1. filtrationAfter filtering off the insoluble matters
  2. concentrationthe solution was concentrated under reduced pressure
  3. customthe crystals of 1-(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)imidazol-2-carboxylic acid thus precipitated
  4. filtrationwere taken up by filtration
  5. additionNext, the crystals were treated by the same method as the one of Example 9

Sources & evidence

ORD record
ord-bc9b806a528542038126b129df3c73c8
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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