Trifluoroacetic acid → HCID 136597083, compound

HRID 1476918Notes

Reaction equation

HRID 1476918 reaction equation
[O:1]=[C:2]1[NH:6][N:5]=[C:4]([C:7]2[N:12]=[C:11]([O:13][C@H:14]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]3)[CH:10]=[CH:9][CH:8]=2)[NH:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:16]1[CH2:17][CH2:18][C@H:14]([O:13][C:11]2[N:12]=[C:7]([C:4]3[NH:3][C:2](=[O:1])[NH:6][N:5]=3)[CH:8]=[CH:9][CH:10]=2)[CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136596926HCID 136596926, compound

Product 1

HCID 136597083HCID 136597083, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude (S)-tert-butyl 3-((6-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyridin-2-yl)oxy)pyrrolidine-1-carboxylate was treated with DCM (4 mL) and TFA (2 mL) for 2 hours at RT and then concentrated. The crude product was purified by preparative HPLC eluting with a gradient of 1-25% ACN in water (acid mode) to give the title compound (125 mg, 14.0% over 3 steps).

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by preparative HPLC
  3. washeluting with a gradient of 1-25% ACN in water (acid mode)

Sources & evidence

ORD record
ord-4b9b722de45644cd9340476e48ffcdb3
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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