Benzenesulfonyl chloride → HCID 68597590, compound

HRID 220538Notes

Reaction equation

HRID 220538 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[C:19]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)=[N:18][CH:17]=[CH:16][N:15]=3)[CH2:10][CH2:9]2)=[C:5]([CH3:27])[NH:4][N:3]=1.[C:28]1([S:34](Cl)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>N1C=CC=CC=1>[C:28]1([S:34]([N:4]2[C:5]([CH3:27])=[C:6]([CH2:7][N:8]3[CH2:13][CH2:12][N:11]([C:14]4[C:19]([C:20]5[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=5)=[N:18][CH:17]=[CH:16][N:15]=4)[CH2:10][CH2:9]3)[C:2]([CH3:1])=[N:3]2)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 59321893HCID 59321893, compound

Product 1

HCID 68597590HCID 68597590, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-(3,5-dimethyl-1H-pyrazol-4-ylmethyl)-3′-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.160 g, 0.4 mmol, 1 eq) add benzenesulfonyl chloride (56 μL, 0.4 mmol) followed by pyridine (1 mL). Heat to 120° C. with stirring for 4 hr. Add water and extract 3 times with ethyl acetate (20 mL), dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 25:75 to 75:25 ethyl acetate:DCM). Lyophilize from a 50% acetonitrile/water solution to give the title compound as a white solid (138 mg, 68%). MS (ES): m/z=507.1 [M+H]+.

Workup

  1. extractionAdd water and extract 3 times with ethyl acetate (20 mL)
  2. dry with materialdry (magnesium sulfate)
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 25:75 to 75:25 ethyl acetate:DCM)

Sources & evidence

ORD record
ord-d4b2c293ff814b9e888ed386b40bcf89
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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