HCID 86683879, compound → HCID 86683880, compound

HRID 1620110Notes

Reaction equation

HRID 1620110 reaction equation
[Cl:1][C:2]1[N:9]=[C:8]([NH:10][C@H:11]([CH3:24])[CH2:12][N:13]2C(=O)C3C(=CC=CC=3)C2=O)[C:7]([F:25])=[CH:6][C:3]=1[C:4]#[N:5]>C(O)C.O1CCCC1>[NH2:13][CH2:12][C@H:11]([NH:10][C:8]1[C:7]([F:25])=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[N:9]=1)[CH3:24]

Participants

3

Reactant 1

HCID 86683879HCID 86683879, compound

Product 1

HCID 86683880HCID 86683880, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Hydrazine•monohydrate (0.124 ml) was added to an ethanol/tetrahydrofuran (5 ml/1 ml) solution containing (R)-2-chloro-6-((1-(1,3-dioxoisoindolin-2-yl)propan-2-yl)amino)-5-fluoronicotinonitrile (300 mg), followed by stirring at room temperature for 14 hours. Further, hydrazine•monohydrate (0.062 ml) was added, followed by stirring at room temperature for 8.5 hours. The solvent was distilled away under reduced pressure, chloroform was added, and insoluble matter was removed. Then, the solvent was distilled away under reduced pressure, and a yellow solid of (R)-6-((1-aminopropan-2-yl)amino)-2-chloro-5-fluoronicotinonitrile (38 mg) was thus obtained.

Workup

  1. stirringby stirring at room temperature for 8.5 hours
  2. distillationThe solvent was distilled away under reduced pressure, chloroform
  3. additionwas added
  4. custominsoluble matter was removed
  5. distillationThen, the solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-4aeb772262be478fa2132ff6afaaded9
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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