Pyridine → HCID 59149953, compound

HRID 655556Notes

Reaction equation

HRID 655556 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.Cl[C:21]([O:24]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl.[CH3:32][C@@H:33]1[NH:38][CH2:37][CH2:36][N:35]([CH2:39][CH2:40][CH2:41][N:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)[C:34]1=[O:48]>C(#N)C>[C:4]1([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:21]([N:38]2[CH2:37][CH2:36][N:35]([CH2:39][CH2:40][CH2:41][N:42]3[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]3)[C:34](=[O:48])[C@@H:33]2[CH3:32])=[O:24])[CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 167173-AminobiphenylHCID 94429TriphosgeneHCID 67079895HCID 67079895, compound

Product 1

HCID 59149953HCID 59149953, compoundYield 176.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

A solution of 3-aminobiphenyl (21 mg, 0.13 mmol) and pyridine (11 mg, 0.14 mmol) in acetonitrile (0.5 ml) was added dropwise at 0° C. to a solution of bis-(trichloromethyl)-carbonate (14 mg, 47 μmol) in acetonitrile (0.5 ml). The reaction mixture was allowed to reach room temperature, then a solution of (S)-3-methyl-1-(3-piperidin-1-yl-propyl)-piperazin-2-one (30 mg, 0.13 mmol) in acetonitrile (0.5 ml) was added dropwise. After 30 min the reaction mixture was evaporated. Chromatography (SiO2; dichloromethane/methanol/25% aq. ammonia solution 90:10:0.25) produced the title compound (36 mg, 66%). Colorless gum, MS (ISP)=435.3 (M+H)+.

Workup

  1. customto reach room temperature
  2. customAfter 30 min the reaction mixture was evaporated

Sources & evidence

ORD record
ord-d8c1c333dbde4f38ac4f4172b4921732
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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