Trifluoroacetic acid → HCID 136596970, compound

HRID 1476797Notes

Reaction equation

HRID 1476797 reaction equation
[O:1]=[C:2]1[NH:6][N:5]=[C:4]([C:7]2[N:8]=[C:9]([O:17][C@@H:18]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]3)[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>CN1C(=O)CCC1>[NH:20]1[CH2:21][CH2:22][C@@H:18]([O:17][C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:16]=[C:7]([C:4]3[NH:3][C:2](=[O:1])[NH:6][N:5]=3)[N:8]=2)[CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136597035HCID 136597035, compound

Product 1

HCID 136596970HCID 136596970, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To crude (R)-tert-butyl 3-((3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)isoquinolin-1-yl)oxy)pyrrolidine-1-carboxylate was added a minimal amount of NMP and TFA (2 mL). The solution was stirred at RT for 10 minutes and concentrated. The crude product was purified by preparative HPLC eluting with a gradient of 15-22% ACN in water (acid mode) to give the title compound (229 mg, 29% over 3 steps).

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by preparative HPLC
  3. washeluting with a gradient of 15-22% ACN in water (acid mode)

Sources & evidence

ORD record
ord-1e887b8ffa4045588839c677972907a1
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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