Triethylamine → HCID 23568903, compound

HRID 2376203Notes

Reaction equation

HRID 2376203 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:22][OH:23])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[N:12]=[C:11]([CH2:22][O:23][S:32]([CH3:31])(=[O:34])=[O:33])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22171056[5-(3,4-Dichlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]methanol

Product 1

HCID 23568903HCID 23568903, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred solution of [5-(3,4-dichlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]-methanol (7.2 g, 0.021 mol) in THF (125 mL) and triethylamine (TEA) (4.6 mL, 0.033 mol) was added methanesulfonyl chloride (2.5 mL, 0.031 mol). The reaction mixture was stirred at 45° C. for 4 h. The reaction mixture was cooled to rt, quenched with H2O (75 mL) then washed with EtOAc (3×50 mL). The organic layer was dried over Na2SO4, filtered and concentrated to oil. This crude pyrazole mesylate was used in the next step without further purification. HPLC: Rt=10.03 (Method E). MS (ES+): mass calculated for C18H18Cl2N2O4S, 427.30; m/z found 428.1 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customquenched with H2O (75 mL)
  3. washthen washed with EtOAc (3×50 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to oil
  7. customThis crude pyrazole mesylate was used in the next step without further purification

Sources & evidence

ORD record
ord-9d2a39e557a04b0f8e7be2996345cfa2
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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