Triethylamine → HCID 178480272, compound

HRID 536744Notes

Reaction equation

HRID 536744 reaction equation
[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:7](=[NH:18])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[F:26][C:27]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:28]=1[C:29](Cl)=[O:30]>C1COCC1>[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][CH:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)/[C:7](=[N:18]/[C:29](=[O:30])[C:28]2[CH:32]=[C:33]([C:36]([F:37])([F:38])[F:39])[CH:34]=[CH:35][C:27]=2[F:26])/[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27348802-Fluoro-5-(trifluoromethyl)benzoyl ChlorideHCID 66643289HCID 66643289, compound

Product 1

HCID 178480272HCID 178480272, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 95E (0.53 g, 2.1 mmol) and Et3N (0.88 mL, 6.3 mmol) in THF (10 mL) was added 2-fluoro-5-(trifluoromethyl)benzoyl chloride (0.320 mL, 2.108 mmol). The mixture was stirred at ambient temperature for 4 h then was quenched with saturated aqueous NaHCO3 (10 mL) and diluted with EtOAc (10 mL). The layers were separated and the aqueous phase was extracted EtOAc (3×10 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by column chromatography (SiO2, 50% hexanes in EtOAc) afforded the title compound (0.48 g, 1.1 mmol, 52% yield). MS (DCI/NH3) m/z 442 (M+H)+.

Workup

  1. customthen was quenched with saturated aqueous NaHCO3 (10 mL)
  2. additiondiluted with EtOAc (10 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted EtOAc (3×10 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by column chromatography (SiO2, 50% hexanes in EtOAc)

Sources & evidence

ORD record
ord-b8d5dc63556b45b5bb1e514dd7ced2a3
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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