Triethylamine → HCID 90203830, compound

HRID 927040Notes

Reaction equation

HRID 927040 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]\[C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1[C:9]([C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][CH:26]=3)=[CH:17][CH:18]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 90204009HCID 90204009, compound

Product 1

HCID 90203830HCID 90203830, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-{4-[(Z)-2-(4-Methanesulfonyl-phenyl)-vinyl]-phenyl}-isoxazol-4-yl)-carbamic acid tert-butyl ester (220 mg, 0.5 mmol) in CH2Cl2 (2 mL) was added triethylamine (0.7 mL, 5 mmol) and 2-nitrobenzenesulfhydrazide (1.0 g, 4.6 mmol). The reaction mixture was stirred for 24 h at rt and then washed with satd NaHCO3 and dried over Na2SO4. Filtration was followed by removal of volatiles over silica gel followed by column chromatography to yield (3-{4-[2-(4-methanesulfonyl-phenyl)-ethyl]-phenyl}-isoxazol-4-yl)-carbamic acid tert-butyl ester (88 mg, 40%) as a white solid.

Workup

  1. washwashed with satd NaHCO3
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration
  4. customwas followed by removal of volatiles over silica gel

Sources & evidence

ORD record
ord-dacfe3a0978540e1af6f72317e7deb91
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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