Isobutylamine → HCID 22933623, compound

HRID 1269854Notes

Reaction equation

HRID 1269854 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]([OH:15])=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH2:20]([NH2:24])[CH:21]([CH3:23])[CH3:22].Cl.CNC.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]([NH:24][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:15])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

8

Reactant 6

HCID 6558IsobutylamineHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 516892Sodium BicarbonateHCID 229333592-(1H-indazol-5-yloxy)benzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 22933623HCID 22933623, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2-(1H-indazol-5-yloxy)benzoic acid (80.6 mg, 0.317 mmol) synthesized in Example 479 and isobutylamine (301 mg, 0.412 mmol) were dissolved in N,N-dimethylformamide (2 ml), and dimethylamine hydrochloride (72.5 mg, 0.380 mmol), hydroxybenzotriazole (47.1 mg, 0.349 mmol) and triethylamine (0.09 ml, 0.634 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-isobutylbenzamide (47 mg, 48%) as a brown solid.

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-6fbf2433d2784b0f84e02667960294a9
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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