1,2-Dichloroethane → 1-(t-Butoxycarbonyl)-cis-3-methoxycarbonyl-5-[N-(1-(4-cyanobenzyl)-1H-imidazol-5-yl)acetylamino]-piperidine

HRID 399120Notes

Reaction equation

HRID 399120 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([NH2:14])[CH2:11][C@H:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19]([C:21]1[CH:36]=[CH:35][C:24]([CH2:25][N:26]2[C:30]([CH2:31][C:32](O)=[O:33])=[CH:29][N:28]=[CH:27]2)=[CH:23][CH:22]=1)#[N:20].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([NH:14][C:32](=[O:33])[CH2:31][C:30]2[N:26]([CH2:25][C:24]3[CH:35]=[CH:36][C:21]([C:19]#[N:20])=[CH:22][CH:23]=3)[CH:27]=[N:28][CH:29]=2)[CH2:11][C@H:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 184336301-(4-Cyanobenzyl)imidazole-5-acetic acidHCID 702740551-tert-Butyl 3-methyl (3S,5R)-5-aminopiperidine-1,3-dicarboxylate

Product 1

HCID 702746181-(t-Butoxycarbonyl)-cis-3-methoxycarbonyl-5-[N-(1-(4-cyanobenzyl)-1H-imidazol-5-yl)acetylamino]-piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(t-Butoxycarbonyl)-cis-3-methoxycarbonyl-5-amino piperidine (134 mg, 0.520 mmol), [1-(4-cyanobenzyl)-1H-imidazol-5-yl]acetic acid (147 mg, 0.520 mmol), HOBT (73,8 mg, 0.546 mmol), EDC (104 mg, 0.546 mmol), and Et3N (65.2 uL, 0.468 mmol) were dissolved in DMF (4 mL) and stirred at ambient temperature overnight. The solution was concentrated under reduced pressure and the residue was chromatographed (silica gel, 0.5-2% MeOH/CH2Cl2 with NH4OH) to give the title compound. 1H NMR (CDCl3) d 7.64 (d, 2H, J=8 Hz), 7.52 (s, 1H), 7.19 (d, 2H, J=8 Hz), 6.90-7.05 (m, 1H), 6.98 (s, 1H), 5.22-5.35 (m, 2H), 3.78-3.91 (m, 2H), 3.69 (s, 3H), 3,57-3.64 (m, 1H), 3.45-3.56 (m, 1H), 3.34 (s, 2H), 3.05-3.30 (m, 1H), 2.55-2.68 (m, 1H), 2.05-2.13 (m, 1H), 1.55-1.70 (m, 1H), 1.42 (s, 9H). FAB MS 482 (M+1)

Workup

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

Sources & evidence

ORD record
ord-5af4eddd1555446f9bd528d361fe5e17
Source dataset
uspto-grants-1998_10
Patent number
US05817678

Reaction notes

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