3,4-Dichlorobenzaldehyde → HCID 135463472, compound

HRID 1786142Notes

Reaction equation

HRID 1786142 reaction equation
[N:1]1([S:6]([CH2:9][C:10](=O)[CH3:11])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH:17]=O.[CH3:23][C:24]1[CH:28]=[C:27]([NH2:29])[NH:26][N:25]=1>N1CCCCC1.O1CCOCC1>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]2[N:26]3[N:25]=[C:24]([CH3:23])[CH:28]=[C:27]3[NH:29][C:10]([CH3:11])=[C:9]2[S:6]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:8])=[O:7])[CH:19]=[CH:20][C:21]=1[Cl:22]

Participants

6

Reactant 3

HCID 227103,4-DichlorobenzaldehydeHCID 57597021HCID 57597021, compoundHCID 178418690HCID 178418690, compound

Product 1

HCID 135463472HCID 135463472, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(pyrrolidin-1-ylsulfonyl)propan-2-one (191 mg, 1.0 mmol), 3,4-dichlorobenzaldehyde (175 mg, 1.0 mmol), 3-methyl-1H-pyrazol-5-amine (97 mg, 1.0 mmol), piperidine (2 drops) and Ti(OPr-i)4 (2 drops) in 1,4-dioxane (4.0 mL) in a sealed tube was stirred at 80° C. for 24 hrs. Solvent was removed and the residue was purified by flash chromatography (silica gel, 0% to 50% ethyl acetate in hexane gradient) to provide 7-(3,4-dichlorophenyl)-2,5-dimethyl-6-(pyrrolidin-1-ylsulfonyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine as a white solid. LC-MS found: (M+1)+=427.10. The two enantiomers were separated with ChiralPAK AS using 20% EtOH-MeOH(1:1) in heptane as mobile phase.

Workup

  1. customSolvent was removed
  2. customthe residue was purified by flash chromatography (silica gel, 0% to 50% ethyl acetate in hexane gradient)

Sources & evidence

ORD record
ord-281e0b038bcd402b86969e2545e33af4
Source dataset
uspto-grants-2009_03
Patent number
US07507730B2

Reaction notes

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