Sodium Bicarbonate → HCID 69373967, compound

HRID 860993Notes

Reaction equation

HRID 860993 reaction equation
[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=[CH:31][C:32]([OH:34])=[O:33])[CH:25]=4)[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:4])=[O:3].[C:35]([O-])(O)=O.[Na+]>>[CH3:35][O:33][C:32](=[O:34])[CH2:31][CH2:30][C:26]1[CH:25]=[C:24]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:16]3[CH:17]=[C:8]([C:5]([S:2]([CH3:1])(=[O:4])=[O:3])([CH3:7])[CH3:6])[CH:9]=[C:10]4[C:15]=3[N:14]=[CH:13][CH:12]=[CH:11]4)[CH:19]=2)[CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 69373271HCID 69373271, compound

Product 1

HCID 69373967HCID 69373967, compound

Conditions

Temperature
100 °C

Procedure

To a solution of 3-{3′-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-biphenyl-3-yl}-acrylic acid methyl ester (1.0 eq.) from EXAMPLE 11, Step 2, in Tol (0.1M) at was added benzenesulfonyl hydrazide (3.8 eq.). The mixture was stirred at 100° C. for 12 h, cooled to rt, poured in saturated aqueous NaHCO3 and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (CH2Cl2:EtOAc; 8.5:1.5) afforded the title compound as a white solid.

Workup

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-213a6a99e44e46ae905b4e3a522005f0
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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