Ammonium Acetate → HCID 178448379, compound

HRID 520348Notes

Reaction equation

HRID 520348 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=O)[CH2:9][NH:10][C:11](=O)[C@@H:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]([CH3:15])[CH3:14])=[N:6][CH:7]=1.C([O-])(=O)C.[NH4+:30]>C1(C)C(C)=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:30]=[C:11]([C@@H:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]([CH3:15])[CH3:14])[NH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 86690073HCID 86690073, compound

Product 1

HCID 178448379HCID 178448379, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

In a sealed tube, a mixture of (S)-tert-butyl 1-(2-(5-bromopyridin-2-yl)-2-oxoethylamino)-3-methyl-1-oxobutan-2-ylcarbamate (0.1 g) and ammonium acetate (0.186 g) in xylene was heated at 130° C. for 3 hrs. The reaction was diluted with EtOAc, washed with sat. NaHCO3, water and sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated to yield a yellow oil. The residue was purified by silica chromatography (0-100% EtOAc in hexane) to yield (S)-tert-butyl 1-(4-(5-bromopyridin-2-yl)-1H-imidazol-2-yl)-2-methylpropylcarbamate (0.06 g) as a pale yellow solid. LC/MS (Cond. N-1): [M+H]+ 395.17, RT=3.06 min.

Workup

  1. washwashed with sat. NaHCO3, water and sat. NaCl
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield a yellow oil
  6. customThe residue was purified by silica chromatography (0-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-c14bcb13a4bf487ba7f4909cc66021cc
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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