Methanesulfonyl chloride → HCID 10456479, compound

HRID 751307Notes

Reaction equation

HRID 751307 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:16]3[CH:17]=[CH:18][C:19]4[N:23]=[CH:22][N:21]([CH2:24][CH2:25][CH2:26][OH:27])[C:20]=4[CH:28]=3)=[C:10]3[CH2:15][CH2:14][CH2:13][N:11]3[N:12]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>N1C=CC=CC=1>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:16]3[CH:17]=[CH:18][C:19]4[N:23]=[CH:22][N:21]([CH2:24][CH2:25][CH2:26][O:27][S:30]([CH3:29])(=[O:32])=[O:31])[C:20]=4[CH:28]=3)=[C:10]3[CH2:15][CH2:14][CH2:13][N:11]3[N:12]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11740079HCID 11740079, compound

Product 1

HCID 10456479HCID 10456479, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Stir a solution of 3-[6-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-benzoimidazol-1-yl]-propan-1-ol (Example 56; 257 mg, 0.67 mmol) and methanesulfonyl chloride (200 μl, 2.06 mmol) in dry pyridine (5 mL) for 2 h. Remove the pyridine in vacuo and dissolve the residue in excess chloroform. Wash the organic layer with saturated sodium bicarbonate and dry over sodium sulfate. Filter and concentrate in vacuo to give the product as a white foam (175 mg, 55%). MS ES+ m/e 452.2 (M+1).

Workup

  1. customRemove the pyridine in vacuo
  2. dissolutiondissolve the residue in excess chloroform
  3. washWash the organic layer with saturated sodium bicarbonate
  4. dry with materialdry over sodium sulfate
  5. filtrationFilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-16e8d9c1e66a474eaa07147af57bfb33
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

Loading…