Malonic Acid → HCID 67169809, compound

HRID 1918348Notes

Reaction equation

HRID 1918348 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:8](C=O)=[CH:9][CH:10]=1)=[O:4].[C:23](O)(=O)[CH2:24][C:25]([OH:27])=[O:26].N1CCCCC1>N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:8]([CH:23]=[CH:24][C:25]([OH:27])=[O:26])=[CH:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 87294983HCID 87294983, compound

Product 1

HCID 67169809HCID 67169809, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound of step 3 of example 428 (400 mg, 1.30 mmol), malonic acid (262 mg, 2.52 mmol) and piperidine (16 mg, 0.19 mmol) were dissolved in pyridine (0.7 ml) and stirred in reflux for 1 h. The material was partitioned between 2N hydrochloric acid and ethyl acetate (product is only sparingly soluble). The combined organic extracts were dried over sodium chloride and evaporated to dryness to yield the title compound.

Workup

  1. temperaturein reflux for 1 h
  2. customThe material was partitioned between 2N hydrochloric acid and ethyl acetate (product
  3. dry with materialThe combined organic extracts were dried over sodium chloride
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-4ee42638d5cb4769b5349eb0769eb3c2
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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