Sodium Bicarbonate → HCID 178527470, compound

HRID 1173107Notes

Reaction equation

HRID 1173107 reaction equation
N[C:2]1[N:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:20]=2[NH:19][CH:18]=[C:17]3[Cl:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.N([O-])=[O:23].[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Cl:21][C:17]1[C:16]2[C:20](=[C:12]([NH:11][S:8]([C:5]3[CH:6]=[N:7][C:2]([OH:23])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH:13]=[CH:14][CH:15]=2)[NH:19][CH:18]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 98186183-Pyridinesulfonamide, 6-amino-N-(3-chloro-1H-indol-7-yl)-HCID 23668193Sodium Nitrite

Product 1

HCID 178527470HCID 178527470, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under ice-cooling, into a solution of the compound of Example 33a (100 mg, 0.31 mmol) dissolved in 2 ml of glacial acetic acid was added dropwise 1 ml of an aqueous solution containing 32 mg (0.46 mmol) of sodium nitrite. After stirring for one hour, the mixture was adjusted to about pH 8 by adding an aqueous sodium bicarbonate and further stirred for 10 minutes. The reaction mixture was extracted with ethyl acetate, and the extract was washed with water, dried over magnesium sulfate and concentrated. Then, the residue was purified by silica gel thin layer chromatography, to give 54 mg of the title compound.

Workup

  1. stirringfurther stirred for 10 minutes
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThen, the residue was purified by silica gel thin layer chromatography

Sources & evidence

ORD record
ord-94c66f15fcc54269b47692b7bfbac555
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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