Trifluoroacetic acid → 4-(2-Chloro-furo[2,3-b]pyrazin-6-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1184689Notes

Reaction equation

HRID 1184689 reaction equation
FC(F)(F)C(O)=O.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]#[C:22][C:23]2[C:28](=[O:29])[N:27](CC3C=CC(OC)=CC=3)[CH:26]=[C:25]([Cl:39])[N:24]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>ClCCl.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[O:29][C:28]3=[N:27][CH:26]=[C:25]([Cl:39])[N:24]=[C:23]3[CH:22]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 679732584-[6-Chloro-4-(4-methoxy-benzyl)-3-oxo-3,4-dihydro-pyrazin-2-ylethynyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866748844-(2-Chloro-furo[2,3-b]pyrazin-6-yl)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Silver triflate (6 mg) and trifluoroacetic acid (0.36 mL) are added to a solution of 4-[6-chloro-4-(4-methoxy-benzyl)-3-oxo-3,4-dihydro-pyrazin-2-ylethynyl]-piperidine-1-carboxylic acid tert-butyl ester (430 mg) in dichloromethane (6 mL). The reaction mixture is stirred at room temperature for 20 min, diluted with dichloromethane and washed with aqueous NaHCO3 solution and brine. The organic phase is dried (MgSO4) and the solvent is evaporated. The residue is chromatographed on silica gel (ethyl acetate/cyclohexane 25:70) to give the title compound as a colorless solid.

Workup

  1. washwashed with aqueous NaHCO3 solution and brine
  2. dry with materialThe organic phase is dried (MgSO4)
  3. customthe solvent is evaporated
  4. customThe residue is chromatographed on silica gel (ethyl acetate/cyclohexane 25:70)

Sources & evidence

ORD record
ord-983338dc71b24cc09513523ac1c366d8
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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