Triethylamine → HCID 58386090, compound

HRID 1963026Notes

Reaction equation

HRID 1963026 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH2:13]O)[C:10]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24]COCC[Si](C)(C)C)=[C:20]([O:33][CH3:34])[CH:19]=3)=[O:16])=[N:9]2)=[CH:4][CH:3]=1.CS([Cl:39])(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[Cl:39][CH2:13][C:11]1[C:10]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:33][CH3:34])[CH:19]=2)=[O:16])=[N:9][N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58386043HCID 58386043, compound

Product 1

HCID 58386090HCID 58386090, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(4-chlorophenyl)-4-(hydroxymethyl)-N-(3-methoxy-4-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)-1H-pyrazole-3-carboxamide (2.11 g, 4.19 mmol) in CH2Cl2 (40 mL) at room temperature under Ar was added methanesulfonyl chloride (0.424 mL, 5.44 mmol) and triethylamine. (1.20 mL, 8.61 mmol). The resulting solution was stirred at room temperature for 1.5 h. Solvent was evaporated. The crude product was diluted with EtOAc (150 mL), washed with H2O (30 mL). The organic layer was separated, dried over MgSO4 and concentrated to give a crude product which was further purified by ISCO automated chromatography (110 g, Hexane/EtOAc, 100:0 to 50:50 gradient) to give the products as beige solid (0.721 g, 44% yield). SEM group was deprotected during the process. LCMS (ES): m/z 392.0 [M+H]+.

Workup

  1. customSolvent was evaporated
  2. additionThe crude product was diluted with EtOAc (150 mL)
  3. washwashed with H2O (30 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a crude product which
  8. customwas further purified by ISCO automated chromatography (110 g, Hexane/EtOAc, 100:0 to 50:50 gradient)

Sources & evidence

ORD record
ord-ed75361d662e463f9dee3457cd1bdf51
Source dataset
uspto-grants-2013_04
Patent number
US08415386B2

Reaction notes

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