1-Aminopiperidine → HCID 11555526, compound

HRID 2112990Notes

Reaction equation

HRID 2112990 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:11]([C:17]([OH:19])=O)[N:10]=[C:9]2[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[Cl:27])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:48]2[CH:49]=[CH:50][CH:51]=C[C:47]=2[N:46]=[N:45]1.NN1CCCCC1>CC#N>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:11]([C:17]([NH:45][N:46]3[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]3)=[O:19])[N:10]=[C:9]2[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[Cl:27])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 166581-AminopiperidineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11517942HCID 11517942, compound

Product 1

HCID 11555526HCID 11555526, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a magnetically stirred suspension of 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfonyl-1H-imidazole-4-carboxylic acid (2.23 g, 5.01 mmol) in anhydrous CH3CN (50 ml) was successively added N,N-diisopropylethylamine (Hunig's base) (1.90 ml, 11.0 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (2.27 g, 5.99 mmol) and 1-aminopiperidine (0.65 ml, 6.03 mmol). After stirring for 16 h, the resulting mixture was concentrated in vacuo. The residue was dissolved in EtOAc, successively washed with aqueous NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated to give a crude solid. This solid was further purified by flash chromatography (silicagel, EtOAc) and triturated with methyl-tert-butyl ether to give 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfonyl-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide in 84% yield,

Workup

  1. concentrationthe resulting mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washsuccessively washed with aqueous NaHCO3 solution, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude solid
  8. customThis solid was further purified by flash chromatography (silicagel, EtOAc)
  9. customtriturated with methyl-tert-butyl ether

Sources & evidence

ORD record
ord-f14a8679125b4ecabecc13e538b22968
Source dataset
uspto-grants-2009_04
Patent number
US07524867B2

Reaction notes

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