Triethylamine → HCID 22933401, compound

HRID 1269855Notes

Reaction equation

HRID 1269855 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](O)=[O:14])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.Cl.[CH3:21][NH:22][CH3:23].Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13]([N:22]([CH3:23])[CH3:21])=[O:14])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 229333592-(1H-indazol-5-yloxy)benzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 22933401HCID 22933401, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2-(1H-indazol-5-yloxy)benzoic acid (80.8 mg, 0.318 mmol) synthesized in Example 479 and dimethylamine hydrochloride (33.7 mg, 0.413 mmol) were dissolved in N,N-dimethylformamide (2 ml), and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (72.5 mg, 0.380 mmol), hydroxybenzotriazole (47.1 mg, 0.349 mmol) and triethylamine (0.13 ml, 0.954 mmol) were added thereto at room temperature and then stirred for 2.5 hours. After the reaction, a saturated aqueous sodium hydrogencarbonate solution was added thereto, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated to obtain 2-(1H-indazol-5-yloxy)-N,N-dimethylbenzamide (51 mg, 57%).

Workup

  1. customAfter the reaction
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8828650fa5464382a795cf6c5b6c295b
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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