Triethylamine → HCID 58975189, compound

HRID 1178953Notes

Reaction equation

HRID 1178953 reaction equation
[CH:1]1([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:22][O:23][C:24](=[O:35])[C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>ClCCl>[CH3:22][O:23][C:24](=[O:35])[C:25]1[CH:26]=[CH:27][C:28]([S:31]([N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[N:7]2)(=[O:32])=[O:33])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4738388Methyl 4-(Chlorosulfonyl)benzoateHCID 178419918HCID 178419918, compound

Product 1

HCID 58975189HCID 58975189, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 3-Cyclopentyl-1H-indazole (2.168 g 11.640 mmole) with triethylamine (3.526 g, 34.92 mmoles) in 50 mls of dichloromethane. Dissolve 4-Chlorosulfonyl-benzoic acid methyl ester (4.085 g, 17.460 mmole) in dichloromethane 50 ml and add drop wise to solution at 0° C. Stir the reaction is for 12 hrs. Dilute the reaction and wash with NaHCO3. Dry organic layer over MgSO4 and concentrate. Purify the residue via column chromatography with a mixture of ethyl acetate and hexanes to isolate 2.046 g (Yield=48.5%) of the title compound: MS ES+385.3.

Workup

  1. additionDilute
  2. customthe reaction
  3. washwash with NaHCO3
  4. concentrationDry organic layer over MgSO4 and concentrate
  5. customPurify the residue via column chromatography
  6. additionwith a mixture of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-42a7c1d0d9f24199b4bb0a61a5726997
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

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