Chlorosuccinimide → HCID 57410023, compound

HRID 2046238Notes

Reaction equation

HRID 2046238 reaction equation
[Cl:1]N1C(=O)CCC1=O.[O:9]([CH2:16][C:17]1[CH:26]=[C:20]2[C:21](=[O:25])[NH:22][CH2:23][CH2:24][N:19]2[N:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[Cl:1][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:16][C:17]2[CH:26]=[C:20]3[C:21](=[O:25])[NH:22][CH2:23][CH2:24][N:19]3[N:18]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 574117992-(phenoxymethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one

Product 1

HCID 57410023HCID 57410023, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

N-chlorosuccinimide (61 mg, 0.45 mmol) was added to a solution of 2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (0.1 g, 0.41 mmol) in CHCl3 (3 mL) and the mixture was stirred at 80° C. for 20 hours. Then the solvent was evaporated in vacuo and the crude product was purified by flash column chromatography (silica; MeOH in DCM 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-(4-chloro-phenoxymethyl)-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (0.1 g, 90% yield).

Workup

  1. customThen the solvent was evaporated in vacuo
  2. customthe crude product was purified by flash column chromatography (silica; MeOH in DCM 0/100 to 10/90)
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-7bbbb2f38e50454ab444ceab56fa8948
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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