Triethylamine → HCID 56933344, compound

HRID 710560Notes

Reaction equation

HRID 710560 reaction equation
[F:1][C:2]([F:7])([CH3:6])[C:3](O)=[O:4].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.ClC1C=C(C=CC=1OC)C[N:34]1[CH2:39][CH2:38][CH:37]([NH:40][C:41]([N:43]2[CH2:48][CH2:47][C:46](=[CH:49][C:50]3[CH:55]=[C:54]([F:56])[CH:53]=[CH:52][C:51]=3[F:57])[CH2:45][CH2:44]2)=[O:42])[CH2:36][CH2:35]1.CCN(CC)CC>C(#N)C.O>[F:57][C:51]1[CH:52]=[CH:53][C:54]([F:56])=[CH:55][C:50]=1[CH:49]=[C:46]1[CH2:47][CH2:48][N:43]([C:41]([NH:40][CH:37]2[CH2:36][CH2:35][N:34]([C:3](=[O:4])[C:2]([F:7])([F:1])[CH3:6])[CH2:39][CH2:38]2)=[O:42])[CH2:44][CH2:45]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27828252,2-Difluoropropionic acidHCID 66691939HCID 66691939, compound

Product 1

HCID 56933344HCID 56933344, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2,2-Difluoropropionic acid (66.0 mg, 0.60 mmol) was dissolved in acetonitrile (2.0 mL), and then HOBt (75.0 mg, 0.60 mmol), WSC (115 mg, 0.60 mmol), the compound (150 mg, 0.40 mmol) obtained in Example 36 (1), and Et3N (167 μL, 1.2 mmol) were added thereto, followed by stirring at room temperature overnight. Water was added to the reaction mixture, and after extraction with chloroform, the extract was washed with water and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporation under reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:30), thereby giving the title compound (20.0 mg, 12%) as a white solid.

Workup

  1. extractionafter extraction with chloroform
  2. washthe extract was washed with water
  3. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. customthe residue obtained by evaporation under reduced pressure
  6. customwas purified

Sources & evidence

ORD record
ord-bb6426f46dd34c87b9cf7cffd48b5e03
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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