Hydrochloric Acid → HCID 68997620, compound

HRID 1821424Notes

Reaction equation

HRID 1821424 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.[O:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[C:35](Cl)=[O:36].[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[O:30][CH:34]=[CH:33][CH:32]=2)=[O:36])=[N:13]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 682422-Furancarbonyl chlorideHCID 68999207HCID 68999207, compound

Product 1

HCID 68997620HCID 68997620, compoundYield 83%

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 furan-2-carbonyl chloride (0.11 mL, 1.1 mmol), followed by stirring for 4 hours. The reaction mixture was extracted with ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was concentrated under reduced pressure to obtain crude product. Further, the product was dissolved in methanol (20 mL) and 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-[(furan-2-carbonyl)amino]benzoic acid (0.31 g, 82%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  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-e8151c5cab5849ca8cda6327d5792461
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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