HCID 68194321, compound → HCID 68194019, compound

HRID 1520148Notes

Reaction equation

HRID 1520148 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]1[C:14]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[N:15][C:16]3[C:21]([N:22]=1)=[CH:20][C:19]([C:23]([O:25]C)=[O:24])=[CH:18][CH:17]=3)[CH2:8][CH2:7][CH2:6]2)#[N:2]>CO.O>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]1[C:14]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)=[N:15][C:16]3[C:21]([N:22]=1)=[CH:20][C:19]([C:23]([OH:25])=[O:24])=[CH:18][CH:17]=3)[CH2:8][CH2:7][CH2:6]2)#[N:2]

Participants

4

Reactant 1

HCID 68194321HCID 68194321, compound

Product 1

HCID 68194019HCID 68194019, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-(6-cyano-1,2,3,4-tetrahydroquinolin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (From Ex 14, step 5, 50 mg, 0.11 mmol) in methanol (20 mL) and water (1 mL) was added lithiumol hydroxide (10 mg, 0.40 mmol) with stifling overnight at room temperature. The resulting mixture was concentrated under vacuum, dissolved in water (10 mL) and adjusted to 7 with AcOH, collected by filtration to give 3-(6-cyano-1,2,3,4-tetrahydroquinolin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a yellow solid (14.7 mg, 30%). [M+H]+ 425.1

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. dissolutiondissolved in water (10 mL)
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-dcd02c67e48447978ebf1e8f4fa55ee0
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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