1,1'-Carbonyldiimidazole → HCID 58573758, compound

HRID 932003Notes

Reaction equation

HRID 932003 reaction equation
[CH2:1]([C@@:4]1([CH3:35])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:32][CH3:33])[CH2:25][NH:26][CH2:27][C:28]([OH:31])([CH3:30])[CH3:29])[C:5]1=[O:34])[CH:2]=[CH2:3].[C:36](N1C=CN=C1)(N1C=CN=C1)=[O:37]>O1CCOCC1>[CH2:1]([C@@:4]1([CH3:35])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[N:6]([C@@H:24]([CH2:32][CH3:33])[CH2:25][N:26]2[CH2:27][C:28]([CH3:29])([CH3:30])[O:31][C:36]2=[O:37])[C:5]1=[O:34])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 68001158HCID 68001158, compound

Product 1

HCID 58573758HCID 58573758, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 42 mg (0.081 mmol) of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(2-hydroxy-2-methylpropylamino)butan-2-yl)-3-methylpiperidin-2-one (Example 100, Step A) in dioxane (2705 μL) was added carbonyldiimidazole (132 mg, 0.812 mmol). The reaction was heated to 100° for 6 h. Purification of the residue by reversed phase HPLC (Sunfire™ Prep C18 OBD 10 μm column (Waters, Milford, Mass.) (eluent: 60 to 85% MeCN/water (0.1% TFA), gradient elution) provided the title compound.

Workup

  1. temperatureThe reaction was heated to 100° for 6 h
  2. customPurification of the residue by reversed phase HPLC (Sunfire™ Prep
  3. washC18 OBD 10 μm column (Waters, Milford, Mass.) (eluent: 60 to 85% MeCN/water (0.1% TFA), gradient elution)

Sources & evidence

ORD record
ord-58697eb8f1cc4082a70091a1632b5ad6
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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