Methanesulfonyl chloride → HCID 68595646, compound

HRID 220539Notes

Reaction equation

HRID 220539 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.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]2[C:14]([N:11]3[CH2:12][CH2:13][N:8]([CH2:7][C:6]4[C:5]([CH3:27])=[N:4][N:3]([S:29]([CH3:28])(=[O:31])=[O:30])[C:2]=4[CH3:1])[CH2:9][CH2:10]3)=[N:15][CH:16]=[CH:17][N:18]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride3×HCID 59321893HCID 59321893, compound

Product 1

HCID 68595646HCID 68595646, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 (0.250 g, 0.7 mmol, 1 eq) add methanesulfonyl chloride (63 μL, 0.8 mmol) followed by pyridine (2 mL). Stir at room temperature for 3 hr. then add a further portion of methanesulfonyl chloride (100 μL, 1.4 mmol, 2 eq). Stir for 2 hr. at room temperature then add yet a further portion of methanesulfonyl chloride (63 μL, 0.8 mmol, 1.2 eq) and then stir at room temperature overnight. Add water (10 mL) and ethyl acetate (10 mL), separate and extract the aqueous layer twice with ethyl acetate (10 mL), dry the combined organic extracts (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with a gradient of 0:100 to 10:90 methanol:DCM), to give the title compound (207 mg, 66%). MS (ES): m/z=445.1 [M+H]+.

Workup

  1. stirringStir for 2 hr
  2. stirringstir at room temperature overnight
  3. customAdd water (10 mL) and ethyl acetate (10 mL), separate
  4. extractionextract the aqueous layer twice with ethyl acetate (10 mL)
  5. dry with materialdry the combined organic extracts (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify (silica gel chromatography
  8. washeluting with a gradient of 0:100 to 10:90 methanol

Sources & evidence

ORD record
ord-11f2141b2baf4e1eabf983def2457c1e
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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