3,4-Dichlorobenzaldehyde → HCID 135463504, compound

HRID 1786137Notes

Reaction equation

HRID 1786137 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12](=O)[CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:15][C:16]1[CH:20]=[C:19]([NH2:21])[NH:18][N:17]=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH:26]=O>C1COCC1.N1CCCCC1>[Cl:22][C:23]1[CH:24]=[C:25]([CH:26]2[N:18]3[N:17]=[C:16]([CH3:15])[CH:20]=[C:19]3[NH:21][C:12]([CH3:13])=[C:11]2[S:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:28]=[CH:29][C:30]=1[Cl:31]

Participants

6

Reactant 3

HCID 227103,4-DichlorobenzaldehydeHCID 13794941HCID 13794941, compoundHCID 178418690HCID 178418690, compound

Product 1

HCID 135463504HCID 135463504, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

1-(4-Fluorophenylsulfonyl)propan-2-one (150 mg, 0.69 mmol), 3-methyl-1H-pyrazol-5-amine (67 mg, 0.69 mmol) and 3,4-dichlorobenzaldehyde (121 mg, 0.69 mmol) were dissolved in THF (5 mL), to which was added a catalytic amount of piperidine (3 drops). The reaction in a sealed tube was stirred at 70° C. for about 48 hrs. After cooling to rt., solvent was removed and crude product was purified by HPLC (acetonitrile-water, 5% to 95% gradient) to provide pure Step B product 7-(3,4-dichlorophenyl)-6-(4-fluorophenylsulfonyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidine as a solid. LC-MS found: (M+1)+=452.17. The two enantiomers were readily separated on Chiral PAK AS using 15% EtOH-MeOH in heptane.

Workup

  1. customThe reaction in a sealed tube
  2. temperatureAfter cooling to rt
  3. custom, solvent was removed
  4. customcrude product was purified by HPLC (acetonitrile-water, 5% to 95% gradient)

Sources & evidence

ORD record
ord-c935895953894e70b1c274db851ad23e
Source dataset
uspto-grants-2009_03
Patent number
US07507730B2

Reaction notes

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