Hydrazine hydrate (1:1) → HCID 178452038, compound

HRID 1476898Notes

Reaction equation

HRID 1476898 reaction equation
[Cl: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]#[N:26])=[CH:7]2.[NH2:27][NH2:28].O>CO>[Cl: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])([CH3:22])[CH3:24])=[O:19])[CH2:14]1)=[N:9][C:8]([C:25]([NH:27][NH2:28])=[NH:26])=[CH:7]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 90387316(S)-tert-butyl 3-((8-chloro-3-cyanoisoquinolin-1-yl)oxy)pyrrolidine-1-carboxylate

Product 1

HCID 178452038HCID 178452038, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (S)-tert-butyl 3-((8-chloro-3-cyanoisoquinolin-1-yl)oxy)pyrrolidine-1-carboxylate (120 mg, 0.32 mmol) in MeOH (50 mL) was added NH2NH2—H2O (5 mL). The resulting mixture was heated to reflux for 2 hours and then cooled and concentrated in vacuo to give the title compound as a yellow solid, which was used without further purification (130.3 mg, 100%). ESI-MS m/z [M+H]+ 406.2.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0447686bb73d40dfb3a81a3b38bf1f0e
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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