Triethylamine → HCID 21919378, compound

HRID 1244446Notes

Reaction equation

HRID 1244446 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH:18](O)[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[C:25]([Cl:27])[CH:26]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.CN(C)C.C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:14](/[CH:17]=[CH:18]/[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[C:25]([Cl:27])[CH:26]=3)(=[O:15])=[O:16])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 10313079Trimethylamine HydrochlorideHCID 21919365HCID 21919365, compound

Product 1

HCID 21919378HCID 21919378, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-{[4-(4-chlorophenyl)piperazin-1-yl]sulfonyl}-4-(5-chloropyridin-3-yl)butan-2-ol (111 mg, 0.25 mmol) in dry CH2Cl2 (2.5 mL) at RT was added under an atmosphere of argon, trimethylamine hydrochloride (2 mg, 0.02 mmol), triethylamine (52 μl, 0.25 mmol), then methanesulfonyl chloride (21 μl, 0.25 mmol). The reaction was stirred for 30 mins at RT, then quenched by addition of saturated aqueous sodium bicarbonate solution (5 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (3×6 mL). The combined organic extracts were then dried, (MgSO4), filtered and concentrated in vacuo. The residue was then dissolved in CH2Cl2 (2.5 mL) and treated with triethylamine (100 μl, 1.36 mmol). After 30 minutes, the reaction was quenched by addition of saturated aqueous sodium bicarbonate solution (5 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (3×6 mL). The combined organic extracts were then dried, (MgSO4), filtered and concentrated in vacuo. The crude material was used in the next step.

Workup

  1. customquenched by addition of saturated aqueous sodium bicarbonate solution (5 mL)
  2. customThe layers were separated
  3. extractionthe aqueous phase extracted with ethyl acetate (3×6 mL)
  4. dry with materialThe combined organic extracts were then dried, (MgSO4),
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was then dissolved in CH2Cl2 (2.5 mL)
  8. waitAfter 30 minutes
  9. customthe reaction was quenched by addition of saturated aqueous sodium bicarbonate solution (5 mL)
  10. customThe layers were separated
  11. extractionthe aqueous phase extracted with ethyl acetate (3×6 mL)
  12. dry with materialThe combined organic extracts were then dried, (MgSO4),
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a0125576b3344f669626ca5da46c62b4
Source dataset
uspto-grants-2006_10
Patent number
US07122551B2

Reaction notes

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