Triethylamine → HCID 178448479, compound

HRID 1931105Notes

Reaction equation

HRID 1931105 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]([CH2:11][CH2:12][CH2:13][CH3:14])[C:7](=[NH:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:16][C:17]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:18]=1[C:19](O)=[O:20].CCN(CC)CC.CCCP(=O)=O>C1COCC1>[CH2:11]([N:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6]/[C:7]/1=[N:15]\[C:19](=[O:20])[C:18]1[CH:22]=[C:23]([C:26]([F:27])([F:28])[F:29])[CH:24]=[CH:25][C:17]=1[F:16])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6882922-Fluoro-5-(trifluoromethyl)benzoic acidHCID 16167369Propylphosphoric anhydrideHCID 66643290HCID 66643290, compound

Product 1

HCID 178448479HCID 178448479, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 92A (315 mg, 1.3 mmol), 2-fluoro-5-(trifluoromethyl)benzoic acid (324 mg, 1.56 mmol), Et3N (543 μL, 3.89 mmol) and propylphosphonic anhydride (927 μL, 1.56 mmol) in THF (15 mL) was stirred at room temperature for 12 hours. The reaction mixture mixture was quenched with NaHCO3 and extracted twice with EtOAc. The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 10-100% EtOAc/hexanes gradient) to afford 228 mg (44%) of the title compound. MS (DCI/NH3) m/z 397 (M+H)+.

Workup

  1. customThe reaction mixture mixture was quenched with NaHCO3
  2. extractionextracted twice with EtOAc
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f05947aa74ff4810a533366e0abe2dfc
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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