Methanesulfonyl chloride → HCID 178505108, compound

HRID 59777Notes

Reaction equation

HRID 59777 reaction equation
Cl.[C:2]1([CH:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@@H:19]4[CH2:24][CH2:23][C@H:22]([CH2:25][NH2:26])[CH2:21][CH2:20]4)[CH:14]=3)[O:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1.O>[C:2]1([CH:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@@H:19]4[CH2:24][CH2:23][C@H:22]([CH2:25][NH:26][S:28]([CH3:27])(=[O:30])=[O:29])[CH2:21][CH2:20]4)[CH:14]=3)[O:9]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 178479230HCID 178479230, compound

Product 1

HCID 178505108HCID 178505108, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 150 mg [cis-4-(2-phenyl-chroman-6-yloxy)-cyclohexylmethyl]amine hydrochloride (0.40 mmol) at room temperature in 4 ml of pyridine 47 μl of methanesulfonyl chloride (0.60 mmol) were added and stirring at room temperature was continued for 16 h. The reaction mixture was diluted with water and extracted with dichloromethane The combined organic layers were washed with diluted aqueous hydrochloric acid, dried with sodium sulfate and filtered, and the solvent removed under reduced pressure. The crude product was purified by reversed phase HPLC. 97 mg of the title compound were isolated as a white solid.

Workup

  1. extractionextracted with dichloromethane The combined organic layers
  2. washwere washed with diluted aqueous hydrochloric acid
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-7ce9a1e6cb9146269f67b0c52e94d24c
Source dataset
uspto-grants-2016_09
Patent number
US09440941B2

Reaction notes

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