Acetonitrile → HCID 86708722, compound

HRID 1751385Notes

Reaction equation

HRID 1751385 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]([C:14](O)=O)[C@@H:12]2[CH2:17][CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].BrCC(C1[CH:35]=[CH:34][C:33]2[C:32]3[C:27](=[CH:28][C:29]([Br:36])=[CH:30][CH:31]=3)[CH2:26][CH2:25][C:24]=2[CH:23]=1)=O.C([N:40]([CH:43]([CH3:45])[CH3:44])CC)(C)C.C(#[N:48])C>C(OCC)(=O)C>[Br:36][C:29]1[CH:28]=[C:27]2[C:32]([C:33]3[CH:34]=[CH:35][C:45]([C:43]4[NH:40][C:14]([C@@H:13]5[C@@H:12]6[CH2:17][C@@H:9]([CH2:10][CH2:11]6)[N:8]5[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N:48][CH:44]=4)=[CH:23][C:24]=3[CH2:25][CH2:26]2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 69673274HCID 69673274, compoundHCID 86708721HCID 86708721, compound

Product 1

HCID 86708722HCID 86708722, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4S)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid (443 mg, 1.83 mmol) and 2-bromo-1-(7-bromo-9,10-dihydrophenanthren-2-yl)ethanone (635 mg, 1.67 mmol) in acetonitrile (7 mL) was added diisopropylethylamine (0.6 mL, 3.34 mmol). The reaction was stirred at room temperature for 16 hours and was then diluted with ethyl acetate. The organics were washed with water and brine, dried (MgSO4) and concentrated. The resulting crude residue was purified by flash chromatography to yield (1R,3S,4S)-tert-butyl 3-(5-(7-bromo-9,10-dihydrophenanthren-2-yl)-1H-imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (670 mg, 74%).

Workup

  1. washThe organics were washed with water and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe resulting crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9d6e03e93a824187abd45f87aaa186fe
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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