Trifluoroacetic acid → HCID 136596944, compound

HRID 1476845Notes

Reaction equation

HRID 1476845 reaction equation
[O:1]=[C:2]1[NH:6][N:5]=[C:4]([C:7]2[N:8]=[C:9]([O:17][CH2:18][C@H:19]3[CH2:23][CH2:22][CH2:21][N:20]3C(OC(C)(C)C)=O)[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[NH:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:20]1[CH2:21][CH2:22][CH2:23][C@@H:19]1[CH2:18][O:17][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:7]([C:4]2[NH:3][C:2](=[O:1])[NH:6][N:5]=2)[N:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136597042HCID 136597042, compound

Product 1

HCID 136596944HCID 136596944, compoundYield 1.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To crude (R)-tert-butyl 2-(((3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)isoquinolin-1-yl)oxy)methyl)pyrrolidine-1-carboxylate was added DCM (3 mL) followed by TFA (2 mL). The mixture was stirred at RT for 2 hours and the solvent was removed in vacuo. The crude product was purified by preparative HPLC eluting with a gradient of 10-25% ACN in water (acid mode) to give the title compound (10 mg, 1.5% over 3 steps). ESI-MS m/z [M+H]+ 312.4.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe crude product was purified by preparative HPLC
  3. washeluting with a gradient of 10-25% ACN in water (acid mode)

Sources & evidence

ORD record
ord-fd5db4399a184a87999d2384ce3b909f
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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