1,2-Dichloroethane → 1-(2,2-Diphenylethyl)-3-[N-(1-(4-cyanobenzyl)-1H-imidazol-5-ylethyl)carbamoyl]piperidine

HRID 399125Notes

Reaction equation

HRID 399125 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH:11]([C:15](O)=[O:16])[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24]([C:26]1[CH:40]=[CH:39][C:29]([CH2:30][N:31]2[C:35]([CH2:36][CH2:37][NH2:38])=[CH:34][N:33]=[CH:32]2)=[CH:28][CH:27]=1)#[N:25].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C>[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH:11]([C:15](=[O:16])[NH:38][CH2:37][CH2:36][C:35]3[N:31]([CH2:30][C:29]4[CH:39]=[CH:40][C:26]([C:24]#[N:25])=[CH:27][CH:28]=4)[CH:32]=[N:33][CH:34]=3)[CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 158510473-(4-Cyanobenzyl) histamineHCID 232911301-(2,2-Diphenylethyl)-3-carboxy piperidine

Product 1

HCID 179300651-(2,2-Diphenylethyl)-3-[N-(1-(4-cyanobenzyl)-1H-imidazol-5-ylethyl)carbamoyl]piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2,2-Diphenylethyl)-3-carboxy piperidine(472 mg, 1,52 mmol),3-(4-cyanobenzyl) histamine (456 mg, 1.52 mmol) (EXAMPLE 1, Step E) HOBT (216 mg, 1.60 mmol), EDC (307 mg, 1.60 mmol), and Et3N (637 uL, 4.57 mmol) were dissolved in DMF (10 mL) and was stirred overnight at ambient temperature. The solution was concentrated under reduced pressure and chromatographed (silica gel, 0.5-2% MeOH/CH2Cl2 with NH4OH) to give the title compound 1H NMR (CDCl3) δ7.96 (br s, 1H), 7.60 d, 2H, J=8 Hz), 7.46 (s, 1H), 7.09-7.37 (m, 12H), 6,74 (s, 1H), 5.20 (s, 2H), 4.26 (t, 1H, J=8 Hz), 3.05-3.17 (m, 2H), 2.93-3.04 (m,1H), 2.78-2.91 (m,2H), 2.49-2,61 (m 1H), 22.40-2.47 (m, 1H), 2.15-2.30 (m, 2H), 1.95-2.14 (m, 2H), 1.86 (d, 1H, J=12 Hz), 1.29-1.55 (m, 3H). FAB MS 518 (M+1)

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customchromatographed (silica gel, 0.5-2% MeOH/CH2Cl2 with NH4OH)

Sources & evidence

ORD record
ord-7eae60b9944d4675a764a5eaa21e61a8
Source dataset
uspto-grants-1998_10
Patent number
US05817678

Reaction notes

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