[3-({5-Chloro-3-[(4-chloro-3-trifluoromethyl-benzene sulfonyl)-methoxymethyl-amino]-pyridin-2-yl}-hydroxy-methyl)-pyridin-2-yl]-carbamic acid tert-butyl ester → HCID 57942364, compound

HRID 1438608Notes

Reaction equation

HRID 1438608 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]1[C:13]([CH:14]([C:16]2[C:21]([N:22]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([C:36]([F:39])([F:38])[F:37])[CH:30]=3)(=[O:28])=[O:27])[CH2:23][O:24][CH3:25])=[CH:20][C:19]([Cl:40])=[CH:18][N:17]=2)[OH:15])=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1.O=[Mn]=O>[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]1[C:13]([C:14]([C:16]2[C:21]([N:22]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([C:36]([F:38])([F:37])[F:39])[CH:30]=3)(=[O:27])=[O:28])[CH2:23][O:24][CH3:25])=[CH:20][C:19]([Cl:40])=[CH:18][N:17]=2)=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 57942296[3-({5-Chloro-3-[(4-chloro-3-trifluoromethyl-benzene sulfonyl)-methoxymethyl-amino]-pyridin-2-yl}-hydroxy-methyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 57942364HCID 57942364, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of [3-({5-chloro-3-[(4-chloro-3-trifluoromethyl-benzene sulfonyl)-methoxymethyl-amino]-pyridin-2-yl}-hydroxy-methyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (750 mg, 1.18 mmol) and MnO2 (512.6 mg, 5.9 mmol) in THF (10 mL) was stirred at 50° C. for overnight. The reaction mixture was cooled to room temperature, filtered through sintered funnel, washed with THF (2×10 mL), dried (anhydrous Na2SO4) and concentrated. The obtained residue was column purified (SiO2, 50% EtOAc-hexanes) to afford (3-{5-chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyrdine-2- carbonyl}-pyridin-2-yl)-carbamic acid tert-butyl ester (456 mg) 61% in yield. ESMS m/z (relative intensity): 635 (M+H)+ (100).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through sintered funnel
  3. washwashed with THF (2×10 mL)
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated
  6. custompurified (SiO2, 50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-ee6ca08973f5457680488e126de74b18
Source dataset
uspto-grants-2009_11
Patent number
US07622583B2

Reaction notes

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