Triethylamine → HCID 90990409, compound

HRID 2390278Notes

Reaction equation

HRID 2390278 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:33][C:34]([F:45])([F:44])[C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:39](=[O:40])[C:38]2[CH:42]=[CH:43][C:35]([C:34]([F:33])([F:44])[F:45])=[CH:36][CH:37]=2)=[CH:22][CH:23]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 58522032HCID 58522032, compound2×

Product 1

HCID 90990409HCID 90990409, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl{2-[(4-aminophenyl)ethynyl]-4-chlorophenoxy}acetate (Intermediate 222; 72 mg; 0.20 mmol) and triethylamine (83 μl; 0.60 mmol) in DCM (2 ml) was treated with 4-(trifluoromethyl)-benzoyl chloride (30 μl; 0.20 mmol). After stirring at RT for 1 hour, the reaction was quenched with a saturated aqueous ammonia solution (1 mL). EtOAc and a saturated NH4Cl solution in water were added, the phases separated and the organic phase was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc to give the title compound.

Workup

  1. customthe reaction was quenched with a saturated aqueous ammonia solution (1 mL)
  2. additionEtOAc and a saturated NH4Cl solution in water were added
  3. customthe phases separated
  4. dry with materialthe organic phase was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by flash column chromatography (silica)
  7. washeluting with cyclohexane containing
  8. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-2aa00e5d19c341bd82c4758b2e456643
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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