Methanesulfonyl chloride → HCID 59434281, compound

HRID 507856Notes

Reaction equation

HRID 507856 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH2:16][CH2:15]1)[CH2:10]2)=[O:5])[CH3:2].[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([N:14]1[CH2:15][CH2:16][CH:17]([N:20]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[S:29]([CH3:28])(=[O:31])=[O:30])[CH2:18][CH2:19]1)[CH2:10]2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11951743HCID 11951743, compound

Product 1

HCID 59434281HCID 59434281, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

3-[4-(4-fluoro-phenylamino)-piperidin-1-yl]-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester (25 mg; 0.07 mmol; 1 eq.) was dissolved in dry prydine (2 mL) and MsCl (19 mg; 2.5 eq.) was added. The reaction mixture was heated to 80° C. and stirred under N2 overnight. The solution was diluted with DCM (10 mL) and washed with saturated NaHCO3 (2×20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under high vacuum to provide the product as an oil. The crude residue was purified by reversed-phase HPLC (2-99% CH3CN/water gradient with 0.05% TFA). LC/MS M/Z 454.2, Retention time=1.88 minutes; 10-99% CH3CN/H2O gradient with 0.05% TFA.

Workup

  1. additionwas added
  2. washwashed with saturated NaHCO3 (2×20 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-dfdb2e26779d4c17a33a2052ede8c18a
Source dataset
uspto-grants-2010_08
Patent number
US07786308B2

Reaction notes

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