Trifluoroacetic acid → HCID 58565378, compound

HRID 2175354Notes

Reaction equation

HRID 2175354 reaction equation
[F:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:3]=1[CH:18]([NH:20]C(=O)OC(C)(C)C)[CH3:19].FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:3]=1[CH:18]([NH2:20])[CH3:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58565374HCID 58565374, compound

Product 1

HCID 58565378HCID 58565378, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl {1-[3-fluoro-1-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]ethyl}carbamate (16 mg, 0.043 mmol) in methylene chloride (1 mL) was added trifluoroacetic acid (0.033 mL, 0.43 mmol). The reaction was stirred at room temperature for 1 hour. The reaction was quenched with saturated NaHCO3 solution and then extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to give the desired amine (11 mg, 94%). LCMS calculated for C15H14F2N3(M+H)+: m/z=274.1. Found: 274.1.

Workup

  1. customThe reaction was quenched with saturated NaHCO3 solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3f7688b1d90042aa96d5708d3f6532ba
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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