7-((1,3-Dioxoisoindolin-2-yl)methyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile → HCID 117668178, compound

HRID 64294Notes

Reaction equation

HRID 64294 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[N:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:26][CH:25]=3)[C:21]([C:22]#[N:23])=[C:17]2[N:16]=[CH:15][CH:14]=1>CO.O1CCOCC1.O.NN>[NH2:3][CH2:12][C:13]1[N:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:26][CH:25]=3)[C:21]([C:22]#[N:23])=[C:17]2[N:16]=[CH:15][CH:14]=1

Participants

5

Reactant 1

HCID 1176682787-((1,3-Dioxoisoindolin-2-yl)methyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Product 1

HCID 117668178HCID 117668178, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 24654Hydrazine hydrate (1:1)CatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7-((1,3-dioxoisoindolin-2-yl)methyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile (290 mg, 0.62 mmol) in 5 mL of MeOH and 5 mL of dioxane was added 12 drops of hydrazine hydrate. The reaction mixture was stirred and heated to 60° C. for 3 hr. The mixture was concentrated and suspended in 20 mL of solvent (DCM/MeOH=10/1). The mixture was filtered and the filtrate was concentrated and purified by the flash chromatography eluting with EA followed by DCM/MeOH (10/1) to give 150 mg (71%) of 7-(aminomethyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile as a solid. MS (ESI) m/e [M+1]+ 342.1.

Workup

  1. concentrationThe mixture was concentrated
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. custompurified by the flash chromatography
  5. washeluting with EA

Sources & evidence

ORD record
ord-e87a42ea2d624bf58da0154037513290
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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