1,1'-Carbonyldiimidazole → (S)-tert-butyl 3-((8-fluoro-3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)isoquinolin-1-yl)oxy)pyrrolidine-1-carboxylate

HRID 1476874Notes

Reaction equation

HRID 1476874 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([O:12][C@H:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1)=[N:9][C:8]([C:25]([NH:27][NH2:28])=[NH:26])=[CH:7]2.C1N=CN([C:34](N2C=NC=C2)=[O:35])C=1>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([O:12][C@H:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:14]1)=[N:9][C:8]([C:25]1[NH:26][C:34](=[O:35])[NH:28][N:27]=1)=[CH:7]2

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178452039HCID 178452039, compound

Product 1

HCID 136596973(S)-tert-butyl 3-((8-fluoro-3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)isoquinolin-1-yl)oxy)pyrrolidine-1-carboxylateYield 47.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of (S)-tert-butyl 3-((8-fluoro-3-(hydrazinyl(imino)methyl)isoquinolin-1-yl)oxy)pyrrolidine-1-carboxylate (500 mg, 1.12 mmol) in dioxane (10 mL) was added CDI (362 mg, 2.24 mmol) and the resulting mixture was heated to reflux for 2 hours. The reaction mixture was concentrated in vacuo to give crude product, which was purified by preparative HPLC to give the title compound (220 mg, 47.4%). ESI-MS m/z [M+H-Boc]+ 316.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto give crude product, which
  5. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-aaa76f092cca48c5bd89d0365c8ca7c4
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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