Trifluoroacetic acid → HCID 67983601, compound

HRID 2173842Notes

Reaction equation

HRID 2173842 reaction equation
C(OC([N:8]([C:24]1[CH:29]=[N:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=2)=[CH:26][N:25]=1)[CH:9]([C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=1)[CH2:10][CH2:11][CH3:12])=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:39][C:36]([F:37])([F:38])[C:33]1[CH:34]=[CH:35][C:30]([C:27]2[N:28]=[CH:29][C:24]([NH:8][CH:9]([C:13]3[CH:14]=[CH:15][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][CH:23]=3)[CH2:10][CH2:11][CH3:12])=[N:25][CH:26]=2)=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68062013HCID 68062013, compound

Product 1

HCID 67983601HCID 67983601, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part A: A round bottom flask was charged with (±)-ethyl 4-(1-((tert-butoxycarbonyl)(5-(4-(trifluoromethyl)phenyl)pyrazin-2-yl)amino)butyl)benzoate (4.85 g, 8.92 mmol), DCM (60 mL) and TFA (15 mL). Reaction mixture stirred at room temperature for 3 hours. Sodium bicarbonate (sat. aq.) used to quench the excess TFA and the aqueous layer is extracted with DCM (3×). Combined organics washed with water (1×), brine (1×), dried over sodium sulfate filtered and concentrated to provide (±)-ethyl 4-(1-((5-(4-(trifluoromethyl)phenyl)pyrazin-2-yl)amino)butyl)benzoate as a crude orange gum (4.01 g, quant.). No further purification before next step. MS (M+1): 444.3.

Workup

  1. customReaction mixture
  2. customto quench the excess TFA
  3. extractionthe aqueous layer is extracted with DCM (3×)
  4. washCombined organics washed with water (1×), brine (1×)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-18e0a07ad0224183a400d330ee0d6b3d
Source dataset
uspto-grants-2015_06
Patent number
US09056834B2

Reaction notes

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