Sodium Bicarbonate → HCID 22674167, compound

HRID 1173145Notes

Reaction equation

HRID 1173145 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.CO.[CH3:25][NH2:26].C(=O)(O)[O-].[Na+]>>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([S:13]([NH:12][C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[C:2]([NH:26][CH3:25])=[N:3][CH:4]=[CH:5]3)(=[O:15])=[O:14])=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 22674120HCID 22674120, compoundHCID 57454252Monomethylamine methanol

Product 1

HCID 22674167HCID 22674167, compoundYield 52%

Procedure

1-Chloro-6-(4-chlorobenzenesulfonylamino)isoquinoline (50 mg, Synthetic Example 61b) and a 40% methylamine methanol solution (5.0 ml) were heated at 130° C. in a sealed tube for 18 hours. After cooling as it was, an aqueous saturated sodium bicarbonate was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent, the residue was purified by silica gel column, to give the title compound (28 mg, 52%) as a pale yellow solid.

Workup

  1. temperatureAfter cooling as it
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter evaporating the solvent
  6. customthe residue was purified by silica gel column

Sources & evidence

ORD record
ord-db8f142e956b4ad5ac1444f91263d853
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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