Tetrahydrofuran → HCID 59170951, compound

HRID 2247483Notes

Reaction equation

HRID 2247483 reaction equation
[NH:1]1CCCC[CH2:2]1.[N:7]1([C:12]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:13]=2C=O)[CH:11]=[CH:10][N:9]=[CH:8]1.[OH-].[Na+].[NH2:24][CH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26]1.[CH2:34]1C[O:37][CH2:36][CH2:35]1>C(OCC)(=O)C.O.C(O)C>[C:2](/[C:35](=[CH:34]\[C:17]1[CH:16]=[CH:13][C:12]([N:7]2[CH:11]=[CH:10][N:9]=[CH:8]2)=[C:19]([O:20][CH3:21])[CH:18]=1)/[C:36]([NH:24][CH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26]1)=[O:37])#[N:1]

Participants

9

Reactant 5

HCID 8028TetrahydrofuranHCID 8082PiperidineHCID 14798Sodium HydroxideHCID 123445(+-)-1-AminoindanHCID 86602483HCID 86602483, compound

Product 1

HCID 59170951HCID 59170951, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cyano ethyl acetate (76.0 μL) and piperidine were added one by one to an ethanol solution (5.0 mL) of 4-(1H-imidazol-1-yl-3-methoxybenzaldehyde (144 mg) obtained in Example 111 (35.0 μL). The reaction solution was refluxed for 3.5 hours, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the crude ester product. 2N sodium hydroxide solution (1.0 mL) was added to a THF (2 mL) solution of the obtained ester product, and the reaction solution was agitated for 45 minutes at room temperature. Then, the reaction solution was warmed up to 50° C., it was agitated for further 9 hours. Crude carboxylic acid sodium salt was obtained by condensing the reaction solution as it was under reduced pressure. 1.0 mg of the title compound was obtained from the obtained carboxylic acid sodium salt and 1-aminoindan (41.0 μL) by the same method as in Example 324. The physical properties of the compound are as follows.

Workup

  1. temperatureThe reaction solution was refluxed for 3.5 hours
  2. customthe organic layer was partitioned
  3. washAfter the obtained organic layer was washed with a saturated saline solution, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain the crude ester product
  7. temperatureThen, the reaction solution was warmed up to 50° C.
  8. stirringit was agitated for further 9 hours
  9. customCrude carboxylic acid sodium salt was obtained by condensing the reaction solution as it

Sources & evidence

ORD record
ord-d57f07a5976a4c2ab5846d4af10cb502
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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