Acetic Acid → HCID 67113605, compound

HRID 1896402

Reaction equation

HRID 1896402 reaction equation
CC1C=CC(S([N:11]2[CH:15]=[C:14]([CH:16]=O)[CH:13]=[N:12]2)(=O)=[O:9])=CC=1.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([OH:28])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.O.O>[OH2:9].[NH:11]1[CH:15]=[C:14]([CH2:16][N:18]2[C:19]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:25][C:26]2=[O:28])[CH:13]=[N:12]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5837762-Aminophenylacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 577430311-tosyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 67113605HCID 67113605, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

In a 100 ml, three-necked flask fitted with a magnetic stirrer, 1-[(4-methylphenyl)sulfonyl]-1H-pyrazole-4-carbaldehyde x58 (1.65 g, 6.6 mmol) is dissolved in a 1/1 mixture of THF/H2O (50 ml) and the solution containing (2-aminophenyl)acetic acid x96 (1 g, 66 mmol) is added. The pH is adjusted to 5 with acetic acid and the mixture is cooled to 0° C. Sodium triacetoxyborohydride (2.10 g, 10 mmol) is added and the mixture is stirred overnight at room temperature. Water is added and the aqueous phase is extracted three times with CH2Cl2. The combined organic phases are washed with brine, dried over MgSO4 and evaporated. Purification of the residue by preparative chromatography on silicagel and recrystallization from AcOEt affords 106 mg of pure 1-(1H-pyrazol-4-ylmethyl)-1,3-dihydro-2H-indol-2-one hydrate 173.

Workup

  1. customIn a 100 ml, three-necked flask fitted with a magnetic stirrer
  2. additionis added
  3. extractionthe aqueous phase is extracted three times with CH2Cl2
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customPurification of the residue by preparative chromatography
  8. customon silicagel and recrystallization from AcOEt

Sources & evidence

ORD record
ord-b78794672abf4d87ad4b87775029e55e
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Linked notes

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