Ethyl formimidate hydrochloride → (3R,5R,6S)-3-((1,3,4-oxadiazol-2-yl)methyl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)piperidin-2-one

HRID 1048245Notes

Reaction equation

HRID 1048245 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([CH2:21][CH:22]3[CH2:24][CH2:23]3)[C:11](=[O:25])[C@@H:10]([CH2:26][C:27]([NH:29][NH2:30])=[O:28])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl.[CH:32](=N)OCC>C1(C)C=CC=CC=1>[O:28]1[CH:32]=[N:30][N:29]=[C:27]1[CH2:26][C@H:10]1[CH2:9][C@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C@@H:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[N:12]([CH2:21][CH:22]2[CH2:23][CH2:24]2)[C:11]1=[O:25]

Participants

4

Reactant 2

HCID 12578842Ethyl formimidate hydrochlorideHCID 565912152-((3R,5R,6S)-5-(3-Chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetohydrazide

Product 1

HCID 56591194(3R,5R,6S)-3-((1,3,4-oxadiazol-2-yl)methyl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)piperidin-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 20 mg (45 μmol) of 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetohydrazide (Example 51) in 0.2 mL of toluene was added ethyl formimidate hydrochloride (6.4 mg, 58 μmol). The reaction mixture was heated to reflux for 14 h and then the reaction was concentrated under reduced pressure. Separation by reversed phase HPLC (10 to 90% AcCN/H2O in 40 min) provided the title compound as a colorless film.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 14 h
  3. concentrationthe reaction was concentrated under reduced pressure
  4. customSeparation by reversed phase HPLC (10 to 90% AcCN/H2O in 40 min)

Sources & evidence

ORD record
ord-1f9e2c228c4b4201b5909b6e4fc71d82
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

Loading…