HCID 86683879, compound → HCID 86683880, compound

HRID 2406758Notes

Reaction equation

HRID 2406758 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-a1f8e37b9f0042ce9f17d4ffa1141171
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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