Iodoethane → HCID 58573996, compound

HRID 932295Notes

Reaction equation

HRID 932295 reaction equation
[CH2:1](I)[CH3:2].[NH2:4][N:5]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C@@H:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[CH2:8][C@@:7]([CH2:26][C:27]([O:29][CH3:30])=[O:28])([CH3:25])[C:6]1=[O:31].[CH3:32][CH2:33]N(C(C)C)C(C)C>CN(C=O)C>[Cl:24][C:20]1[CH:19]=[C:18]([C@@H:9]2[C@@H:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[N:5]([N:4]([CH2:1][CH3:2])[CH2:32][CH3:33])[C:6](=[O:31])[C@:7]([CH2:26][C:27]([O:29][CH3:30])=[O:28])([CH3:25])[CH2:8]2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 58573862HCID 58573862, compound

Product 1

HCID 58573996HCID 58573996, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl iodide (67.1 μL, 0.831 mmol) was added to a solution of methyl 2-((3R,5R,6S)-1-amino-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetate (Example 429, step B, 35 mg, 0.083 mmol) and DIEA (145 μL, 0.831 mmol) in DMF. The resulting mixture was stirred at 80° C. for 12 h. The mixture was concentrated and purified by reversed phase HPLC (Sunfire™ Prep C18 OBD 10 μm column; Waters, Milford, Mass.; 40-90% water/acetonitrile gradient with 0.1% TFA). Desired fractions were pooled and concentrated to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by reversed phase HPLC (Sunfire™ Prep C18 OBD 10 μm column; Waters, Milford, Mass.; 40-90% water/acetonitrile gradient with 0.1% TFA)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-886367df62984edbaa66cba365696fbd
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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