Triethylamine → HCID 10298944, compound

HRID 1062427Notes

Reaction equation

HRID 1062427 reaction equation
[CH2:1]([C:5]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[N:7][C:6]=1[C:24](Cl)=[O:25])[CH2:2][CH2:3][CH3:4].[NH2:27][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.CCN(CC)CC>C(Cl)Cl>[CH2:1]([C:5]1[N:9]([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[N:7][C:6]=1[C:24]([NH:27][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:25])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 166581-AminopiperidineHCID 22285450HCID 22285450, compound

Product 1

HCID 10298944HCID 10298944, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-butyl-2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carbonyl chloride (227 mg, 0.56 mmol) in CH2Cl2 (5 mL), were added 1-aminopiperidine (113 mg, 1.12 mmol) and Et3N (234 μL, 1.68 mmol). The solution was stirred overnight at rt, and then the solvents were evaporated under reduced pressure. The residue was purified by preparative reversed-phase HPLC, using 20 to 100% MeCN in water as gradient, to provide 125 mg (48%) of 5-butyl-2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-(1-piperidinyl)-1H-imidazole-4-carboxamide as a white powder. 1H NMR (400 MHz, CDCl3) δ 7.49-7.27 (m, 8 H), 2.93 (t, 2 H), 2.82 (bs, 4 H), 1.77-1.71 (m, 4 H), 1.46-1.37 (m, 4 H), 1.25-1.20 (2 H), 0.79 (t, 3 H). LC-MS m/z 471.33 (MH+), retention time 2.88 min (method 2).

Workup

  1. customthe solvents were evaporated under reduced pressure
  2. customThe residue was purified by preparative reversed-phase HPLC

Sources & evidence

ORD record
ord-b4ebfa792bc8424f96e18afd83341951
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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