Hydrochloric Acid → HCID 68999490, compound

HRID 1821423Notes

Reaction equation

HRID 1821423 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][N:13]=2)=[C:6]([NH2:21])[CH:5]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[OH-].[Na+].Cl>C1COCC1.CO>[NH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12](/[CH:11]=[CH:10]/[C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:22])=[CH:5][C:6]=2[NH:21][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:13]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 68999207HCID 68999207, compound

Product 1

HCID 68999490HCID 68999490, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-amino-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid methyl ester (0.30 g, 1.0 mmol) obtained in Step 1 of Example 217 and triethylamine (0.43 ml, 3.1 mmol) in THF (10 mL) was added with benzoyl chloride (0.13 mL, 1.1 mmol) followed by stirring for 4 hours. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and concentrated under reduced pressure to obtain crude product. Further, the product was dissolved in methanol (20 mL) and the solution was added with 2 mol/L aqueous sodium hydroxide solution (5.0 mL), followed by stirring at 60° C. for 1 hour. The reaction mixture was acidified by hydrochloric acid (6 mol/L) and the precipitated crystal was collected by filtration to obtain (E)-4-[2-(1H-indazol-3-yl)vinyl]-3-(benzoylamino)benzoic acid (0.35 g, 89%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution
  3. concentrationconcentrated under reduced pressure
  4. customto obtain crude product
  5. stirringby stirring at 60° C. for 1 hour
  6. filtrationthe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-d840aa89bbef402d8ef83d6fd8c9101d
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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