Hydrochloric Acid → HCID 69002294, compound

HRID 1821422Notes

Reaction equation

HRID 1821422 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.[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[C:35](Cl)=[O:36].C(=O)([O-])O.[Na+].[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:35]([C:31]2[S:30][CH:34]=[CH:33][CH:32]=2)=[O:36])=[N:13]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 789282-Thiophenecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 68999207HCID 68999207, compound

Product 1

HCID 69002294HCID 69002294, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-amino-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid methyl ester (0.51 g, 1.8 mmol) obtained in Step 1 of Example 217 and triethylamine (0.73 ml, 5.3 mmol) in THF (20 mL) was added with 2-thiophenecarbonyl chloride (0.20 g, 1.9 mmol) and stirred for 2 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to obtain crude product. Further, the product was dissolved in methanol (10 mL) and 2 mol/L aqueous sodium hydroxide solution (2.0 mL) was added thereto, 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-[(thiophen-2-ylcarbonyl)amino]benzoic acid (0.28 g, 41%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customto obtain crude product
  4. stirringby stirring at 60° C. for 1 hour
  5. filtrationthe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-3e2d540e69f949159361c0103b82564f
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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