1,1'-Carbonyldiimidazole → HCID 136597037, compound

HRID 1476908Notes

Reaction equation

HRID 1476908 reaction equation
[NH:1]([C:3](=[NH:29])[C:4]1[N:5]=[C:6]([NH:16][C@H:17]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]2)[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[O:14][CH3:15])[NH2:2].C1N=CN([C:35](N2C=NC=C2)=[O:36])C=1>O1CCOCC1>[CH3:15][O:14][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[C:6]([NH:16][C@H:17]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:18]1)=[N:5][C:4]([C:3]1[NH:29][C:35](=[O:36])[NH:2][N:1]=1)=[CH:13]2

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178488615HCID 178488615, compound

Product 1

HCID 136597037HCID 136597037, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of (S)-tert-butyl 3-((3-(hydrazinyl(imino)methyl)-8-methoxyisoquinolin-1-yl)amino)pyrrolidine-1-carboxylate (400 mg, 1.0 mmol) in dioxane (10 mL) was added CDI (245 mg, 1.5 mmol). The resulting mixture was heated to reflux for 2 hours and then concentrated in vacuo. The crude product was purified by preparative HPLC to give the title compound (80 mg, 18% over 2 steps). ESI-MS m/z [M+H]+ 427.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-ae285be1e3be42dba6b7e8539ea57087
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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