Methanesulfonyl chloride → N-(3-(6-chloro-4-iodopyridin-2-ylamino)cyclohexyl)methanesulfonamide

HRID 390102

Reaction equation

HRID 390102 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH:11]([NH2:15])[CH2:10]2)[CH:5]=[C:4]([I:16])[CH:3]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>N1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][S:18]([CH3:17])(=[O:20])=[O:19])[CH2:10]2)[CH:5]=[C:4]([I:16])[CH:3]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86649873N1-(6-chloro-4-iodopyridin-2-yl)cyclohexane-1,3-diamine

Product 1

HCID 87178324N-(3-(6-chloro-4-iodopyridin-2-ylamino)cyclohexyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of EXAMPLE 11A (100 mg, 0.3 mmol) in pyridine (5 mL) was added methanesulfonyl chloride (50 mg, 0.4 mmol). The mixture was stirred at ambient temperature for 5 h and partitioned between ethyl acetate and brine. The organic phase was washed with brine and concentrated. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate to provide the title compound. Yield: 100 mg (82%). MS (DCI/NH3) m/z 430 (M+H)+.

Workup

  1. custompartitioned between ethyl acetate and brine
  2. washThe organic phase was washed with brine
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-9a914a045aa04c59866671a9903bff04
Source dataset
uspto-grants-2013_02
Patent number
US08383624B2

Linked notes

Loading…