Sodium Bicarbonate → HCID 23130651, compound

HRID 2080207Notes

Reaction equation

HRID 2080207 reaction equation
[NH2:1][C:2]1[N:23]=[CH:22][C:21](N)=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].N([O-])=O.[Na+].[C:29](=O)(O)[O-:30].[Na+]>S(=O)(=O)(O)O.CO>[NH2:1][C:2]1[N:23]=[C:22]([O:30][CH3:29])[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 23130529HCID 23130529, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23130651HCID 23130651, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

2,5-Diamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Preparation Example A+-10 (27 mg, 59 μmol), sodium nitrite (4.1 mg, 59 μmol) and sulfuric acid (several drops) were dissolved in methanol (5 mL), and the solution was stirred for 30 minutes under reflux. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, and the organic layer was washed with brine. The solvent was evaporated in vacuo, the residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), then, further by NH silica gel column chromatography (hexane:ethyl acetate=5:1), and the title compound (0.7 mg) was obtained as a white solid.

Workup

  1. temperatureunder reflux
  2. extractionwhich was then extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used)

Sources & evidence

ORD record
ord-8bc32b526608496cbf91a8f5c6c7a792
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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