Aniline → HCID 57733416, compound

HRID 1920760Notes

Reaction equation

HRID 1920760 reaction equation
O=[C:2]([CH2:25][CH3:26])[CH:3]([C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](O)=[O:19])[C:4](=[O:15])[NH:5][C@H:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:7][CH3:8].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(#N)C>[C:9]1([C@@H:6]([NH:5][C:4]([C:3]2[C:16]3[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:18](=[O:19])[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:2]=2[CH2:25][CH3:26])=[O:15])[CH2:7][CH3:8])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 57733384HCID 57733384, compound

Product 1

HCID 57733416HCID 57733416, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A sealed mixture of 2-[2-oxo-1-((S)-1-phenyl-propylcarbamoyl)-butyl]-benzoic acid (82 mg, 0.2 mmol) and aniline (0.3 ml, 3.3 mmol) in acetonitrile (0.3 ml) was heated under microwave irradiation at +160° C. for 10 min. The mixture was partitioned between ethyl acetate (20 ml) and 3M aq. HCl (2×8 ml), sat. aq. NaHCO3 (2×10 ml and brine, dried (MgSO4) and evaporated. The residue was purified by flash chromatography (SiO2, gradient heptane-ethyl acetate) to give 32 mg of the title compound. LC-MS (m/z) 411.5 (MH+); tR=1.48. 1H NMR (500 MHz, DMSO-d6): a mixture of two atropisomers.

Workup

  1. temperaturewas heated under microwave irradiation at +160° C. for 10 min
  2. customThe mixture was partitioned between ethyl acetate (20 ml) and 3M aq. HCl (2×8 ml), sat. aq. NaHCO3 (2×10 ml and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography (SiO2, gradient heptane-ethyl acetate)

Sources & evidence

ORD record
ord-cb21015c5fe648ffaa913915514b100d
Source dataset
uspto-grants-2012_05
Patent number
US08173639B2

Reaction notes

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