Methanesulfonyl chloride → HCID 23383640, compound

HRID 1636053Notes

Reaction equation

HRID 1636053 reaction equation
[OH:1][CH:2]([CH3:31])[CH:3]([N:5]1[C:9](=[O:10])[N:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH:7]=[N:6]1)[CH3:4].[CH3:32][S:33](Cl)(=[O:35])=[O:34]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:32][S:33]([O:1][CH:2]([CH3:31])[CH:3]([N:5]1[C:9](=[O:10])[N:8]([C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH2:18][CH2:19][N:20]([C:23]4[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=4)[CH2:21][CH2:22]3)=[CH:15][CH:16]=2)[CH:7]=[N:6]1)[CH3:4])(=[O:35])=[O:34]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 22743447HCID 22743447, compound

Product 1

HCID 23383640HCID 23383640, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6344DichloromethaneSolvent2×

Procedure

N,N-dimethyl-4-pyridinamine (0.01062 mol) and intermediate 5a (0.00708 mol) were suspended in CH2Cl2 (50 ml). A solution of methanesulfonylchloride (0.01062 mol) in CH2Cl2 (30 ml) was added dropwise at room temperature. The mixture was stirred at room temperature for the weekend. N,N-dimethyl-4-pyridinamine (0.00352 mol) and methanesulfonylchloride (0.00358 mol) were added again. The mixture was stirred overnight, washed with water (2×100 ml), dried, filtered over decalite and the solvent was evaporated. The residue was dissolved in MIK (150 ml). Activated charcoal (0.5 g) was added. The mixture was boiled, filtered warm and stirred for 2 hours. The precipitate was filtered off and dried, yielding 1.7 g (50%) of [S-(R*,S*)]-2,4-dihydro-2-(2-methanesulfonyloxy-1-methylpropyl)-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one (interm. 5d).

Workup

  1. stirringThe mixture was stirred overnight
  2. washwashed with water (2×100 ml)
  3. customdried
  4. filtrationfiltered over decalite
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in MIK (150 ml)
  7. additionActivated charcoal (0.5 g) was added
  8. filtrationfiltered
  9. temperaturewarm
  10. stirringstirred for 2 hours
  11. filtrationThe precipitate was filtered off
  12. customdried

Sources & evidence

ORD record
ord-9b9ff6fb6b274819928adbe8dc6e0bf9
Source dataset
uspto-grants-2003_01
Patent number
US06512116B2

Reaction notes

Loading…