Trifluoroacetic acid → Trifluoroacetic acid

HRID 2209079Notes

Reaction equation

HRID 2209079 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:8]1([N:11]2[C:15]3[C:16]([O:32][C@@H:33]([C@H:35]4[CH2:39][NH:38][C:37](=[O:40])[CH2:36]4)[CH3:34])=[N:17][C:18]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)=[CH:22][CH:21]=4)=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH2:10][CH2:9]1.C(N(CC)CC)C.FC(F)(F)S(OCC(F)F)(=O)=O>C(Cl)Cl>[CH:8]1([N:11]2[C:15]3[C:16]([O:32][C@@H:33]([C@H:35]4[CH2:39][NH:38][C:37](=[O:40])[CH2:36]4)[CH3:34])=[N:17][C:18]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:31][CH2:30][N:29]([CH2:3][CH:2]([F:7])[F:1])[CH2:28][CH2:27]5)=[CH:22][CH:21]=4)=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH2:9][CH2:10]1.[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 117844129HCID 117844129, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 117843654HCID 117843654, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an appropriate sized vial the trifluoroacetic acid salt of (R)-4-((R)-1-((3-cyclopropyl-6-(4-(piperazin-1-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one 3.42 (25 mg, 0.044 mmol) and triethylamine (27 mg, 0.27 mmol) were dissolved in DCM (1.5 mL). To this mixture 2,2-difluoroethyl trifluoromethanesulfonate (11 mg, 0.051 mmol) was added and mixture was stirred at room temperature for 30 min. The solution was concentrated under reduced pressure and the residue was purified via prep HPLC (2-65% acetonitrile in water, 0.1% trifluoroacteic acid) to isolate (R)-4-((R)-1-((3-cyclopropyl-6-(4-(4-(2,2-difluoroethyl)piperazin-1-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one 3.46 as a trifluoroacetic acid salt.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe residue was purified via prep HPLC (2-65% acetonitrile in water, 0.1% trifluoroacteic acid)

Sources & evidence

ORD record
ord-92ca2d68062642beabc500da4590b40a
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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