Sodium Bicarbonate → 4-chloro-2,5-difluoro-N-[(1R)-2,2,2-trifluoro-1-methylethyl]benzamide

HRID 2363327Notes

Reaction equation

HRID 2363327 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([F:12])[CH:3]=1.Cl.[F:14][C:15]([F:20])([F:19])[C@H:16]([NH2:18])[CH3:17].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([NH:18][C@H:16]([CH3:17])[C:15]([F:20])([F:19])[F:14])=[O:7])=[C:4]([F:12])[CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27364984-Chloro-2,5-difluorobenzoyl chlorideHCID 44593757(2R)-1,1,1-Trifluoropropan-2-amine--hydrogen chloride (1/1)

Product 1

HCID 866757524-chloro-2,5-difluoro-N-[(1R)-2,2,2-trifluoro-1-methylethyl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-2,5-difluorobenzoyl chloride (29.6 mg, 0.140 mmol) (Oakwood, Cat. #: 001628) was added to a solution of (2R)-1,1,1-trifluoropropan-2-amine hydrochloride (20.0 mg, 0.134 mmol) (SynQuest Lab, Cat. #: 3130-7-R1) in methylene chloride (4.0 mL) at 0° C. The reaction mixture was stirred at room temperature for 30 min., then worked up with saturated aqueous NaHCO3, and extracted with dichloromethylene. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford the desired product which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=288.0/289.9.

Workup

  1. extractionextracted with dichloromethylene
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85e697f89b854045b75bc8a0fa5fc955
Source dataset
uspto-grants-2014_04
Patent number
US08691807B2

Reaction notes

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