5-Chlorovaleryl chloride → HCID 69192083, compound

HRID 1034977Notes

Reaction equation

HRID 1034977 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9]#[N:10].[Cl:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17]>N1C=CC=CC=1>[Cl:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9]#[N:10])=[O:17]

Participants

4

Reactant 2

HCID 740895-Chlorovaleryl chlorideHCID 2198705-amino-1,3-dimethyl-1H-pyrazole-4-carbonitrile

Product 1

HCID 69192083HCID 69192083, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-amino-1,3-dimethyl-1H-pyrazole-4-carbonitrile (1.59 g, 11.67 mmol) in anhydrous pyridine (15 mL) was slowly added 5-chlorovaleryl chloride (1.80 mL, 14.0 mmol) at 0° C. After addition, the reaction mixture was allowed to warm up to rt and stir at rt overnight. The reaction mixture was concentrated on a rotavapor and the residue was partitioned between ethyl acetate and brine. The organic phase was washed with brine and concentrated. The residue was separated by flash chromatography (silica gel, 50-80% gradient EtOAc in hexane) to provide Example 96A. Yield: 2.42 g (81%). MS (DCI): m/z 255 (M+H)+.

Workup

  1. customat 0° C
  2. additionAfter addition
  3. concentrationThe reaction mixture was concentrated on a rotavapor
  4. customthe residue was partitioned between ethyl acetate and brine
  5. washThe organic phase was washed with brine
  6. concentrationconcentrated
  7. customThe residue was separated by flash chromatography (silica gel, 50-80% gradient EtOAc in hexane)
  8. customto provide Example 96A

Sources & evidence

ORD record
ord-7fa01b2f19a044f5bebf46ffb88ccd33
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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