HCID 90418928, compound → HCID 90419031, compound

HRID 514860Notes

Reaction equation

HRID 514860 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([S:13]([NH:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)(=[O:15])=[O:14])[CH:6]=[C:7](Cl)[CH:8]=2)[N:3]=1>CO.[Pd]>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([S:13]([NH:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)(=[O:15])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 1

HCID 90418928HCID 90418928, compound

Product 1

HCID 90419031HCID 90419031, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(2-amino-6-chloroquinoline-8-sulfonamido)benzoic acid (150 mg, 0.44 mmol), 10% Pd/C (20 mg) in methanol (5 mL) was stirred under H2 atmosphere overnight when LCMS indicated that the reaction was complete. The resulting mixture was filtered, and the filtrate was concentrated to yield 100 mg of title compound, which was used in the next step without further purification. LCMS (m/z): 344.6 (M+1)+

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5d5390156420454a90b094a4e65a9d06
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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