Diisopropylethylamine → tert-butyl 2-(N-(4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate

HRID 923599Notes

Reaction equation

HRID 923599 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:31]=[CH:30][C:8]([CH2:9][N:10]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)=[NH:4].CCN(C(C)C)C(C)C.[CH3:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:53]=[CH:52][C:51]([C:54](Cl)=O)=[CH:50][CH:49]=2)=[CH:44][CH:43]=1>CC(=O)OCC>[CH3:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:53]=[CH:52][C:51]([C:54]3[O:1][N:2]=[C:3]([C:5]4[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH2:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[C:11](=[O:21])[C:12]5[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=5)=[CH:30][CH:31]=4)[N:4]=3)=[CH:50][CH:49]=2)=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 140418444'-Methyl-[1,1'-biphenyl]-4-carbonyl chlorideHCID 178451242HCID 178451242, compound

Product 1

HCID 71111626tert-butyl 2-(N-(4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetateYield 73.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared using General Procedure 20. To a stirred solution of tert-butyl 2-(N-(4-(N-hydroxycarbamimidoyl)benzyl)-4-nitrobenzamido)acetate (7.25 g, 16.6 mmol) INT-57 in dioxanes (25 mL) was added DIEA (3.19 mL, 18.24 mmol) then 4′-methyl-[1,1′-biphenyl]-4-carbonyl chloride (3.83 g, 16.6 mmol). The reaction mixture was stirred at room temperature for 30 mins then at 120° C. for 3 h. The reaction mixture was allowed to cool to room temperature, diluted with EA (400 mL) and washed with brine (500 mL). The organics were pre-absorbed onto silica gel and purified by chromatography (MeCN/DCM) to provide 7.35 g (73%) of tert-butyl 2-(N-(4-(5-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate INT-58 as a white powder. LCMS-ESI (m/z) calculated for C35H32N4O6: 604; found 549 [M-t-Bu+H]+, tR=3.24 min (Method 10).

Workup

  1. customPrepared
  2. waitat 120° C. for 3 h
  3. temperatureto cool to room temperature
  4. washwashed with brine (500 mL)
  5. customThe organics were pre-absorbed onto silica gel
  6. custompurified by chromatography (MeCN/DCM)

Sources & evidence

ORD record
ord-edee71d9cc884dbfb75d0786dc65a027
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

Loading…