Sodium Bicarbonate → HCID 22674167, compound

HRID 1005702Notes

Reaction equation

HRID 1005702 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%

Conditions

Temperature
130 °C

Procedure

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

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-1705f4117e75436c880647633d7d1434
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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