Trifluoroacetic acid → HCID 58548004, compound

HRID 2207779Notes

Reaction equation

HRID 2207779 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:15][CH:14]([O:16][C:17]2[C:18]([C:23]3[CH2:24][N:25](C(OC(C)(C)C)=O)[CH2:26][CH2:27][CH:28]=3)=[N:19][CH:20]=[CH:21][N:22]=2)[CH2:13]1)=[O:11].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:13][CH:14]([O:16][C:17]2[C:18]([C:23]3[CH2:24][NH:25][CH2:26][CH2:27][CH:28]=3)=[N:19][CH:20]=[CH:21][N:22]=2)[CH2:15]1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54671336HCID 54671336, compound

Product 1

HCID 58548004HCID 58548004, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(3-(1-(1H-benzo[d]imidazole-2-carbonyl)azetidin-3-yloxy)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (see EXAMPLE 10.72; 120 mg, 0.252 mmol) in DCM (2 mL) is added 2,2,2-trifluoroacetic acid (116 μL, 1.511 mmol). The reaction was stirred at room temperature 24 hours. The reaction was concentrated, and the residue dissolved in MeOH (2 mL) and applied to a Varian SCX ion exchange column (1 g). The salt was eluted with MeOH (2×5 mL) and the product eluted with 2.0 M NH3 in MeOH (2×5 mL). The NH3 containing fractions were concentrated to give the crude amine which was carried on to the next step without further purification.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue dissolved in MeOH (2 mL)
  3. washThe salt was eluted with MeOH (2×5 mL)
  4. washthe product eluted with 2.0 M NH3 in MeOH (2×5 mL)
  5. concentrationThe NH3 containing fractions were concentrated

Sources & evidence

ORD record
ord-91fad0297bc24d398fbe592b9c56019e
Source dataset
uspto-grants-2016_06
Patent number
US09376450B2

Reaction notes

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