Hydrochloric Acid → 5-Chloro-6-(2-chloro-4-fluorophenyl)-7-(4-methylpiperidin-1-yl)-3-methylmercapto-pyrazolo [2,3-a]pyrimidine

HRID 1866085Notes

Reaction equation

HRID 1866085 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Cl:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[Cl:19])=[C:10]([N:20]2[CH2:25][CH2:24][CH:23]([CH3:26])[CH2:22][CH2:21]2)[N:9]2[N:27]=[CH:28][CH:29]=[C:8]2[N:7]=1.[CH3:30][S:31](OC)(=O)=S.Cl>ClCCl>[Cl:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[Cl:19])=[C:10]([N:20]2[CH2:25][CH2:24][CH:23]([CH3:26])[CH2:22][CH2:21]2)[N:9]2[N:27]=[CH:28][C:29]([S:31][CH3:30])=[C:8]2[N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 14573333Methyl methylthiosulphonateHCID 866003145-Chloro-6-(2-chloro-4-fluorophenyl)-7-(4-methylpiperidin-1-yl)pyrazolo[2,3-a]pyrimidine

Product 1

HCID 579774485-Chloro-6-(2-chloro-4-fluorophenyl)-7-(4-methylpiperidin-1-yl)-3-methylmercapto-pyrazolo [2,3-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

With stirring, 1.06 g of aluminium trichloride were initially added to 1 g of 5-chloro-6-(2-chloro-4-fluorophenyl)-7-(4-methylpiperidin-1-yl)pyrazolo[2,3-a]pyrimidine, the preparation of which is described, for example, in WO 02/048151, in 50 ml of dichloromethane, and 0.99 g of methyl methylthiosulphonate was then added dropwise. After 15 h of stirring at room temperature, the mixture was poured into ice-water and hydrochloric acid was added. The organic phase was separated off, and the aqueous phase was extracted two more times with in each case 15 ml of ethyl acetate. The combined organic phases were dried with sodium sulphate, and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel using cyclohexane/ethyl acetate 4:1. This gave 0.65 g of an orange oil, logPs=5.73.

Workup

  1. customthe preparation of which
  2. stirringAfter 15 h of stirring at room temperature
  3. additionwas added
  4. customThe organic phase was separated off
  5. extractionthe aqueous phase was extracted two more times with in each case 15 ml of ethyl acetate
  6. dry with materialThe combined organic phases were dried with sodium sulphate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-9999fd6842d74a18972790ed93266ef8
Source dataset
uspto-grants-2009_12
Patent number
US07629294B2

Reaction notes

Loading…