Diisopropylethylamine → 1-(4'-Cyanobenzyl)imidazol-5-ylmethyl piperazine-4-carboxylic acid-(2,2-dimethyl)propyl ester

HRID 276788Notes

Reaction equation

[C:1]([C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]2[CH2:14][C:15]2[NH:19][CH:18]=[N:17][CH:16]=2)=[CH:5][CH:4]=1)#[N:2].CCN(C(C)C)C(C)C.Cl[C:32]([O:34][CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:33]>C(Cl)Cl>[CH3:37][C:36]([CH3:39])([CH3:38])[CH2:35][O:34][C:32]([N:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:21][CH:20]=2)[CH:9]([CH2:14][C:15]2[NH:19][CH:18]=[N:17][CH:16]=2)[CH2:10]1)=[O:33]

Participants

Conditions

Temperature: 25 °C

Procedure

To 1-(4′-Cyanobenzyl)imidazol-5-ylmethyl piperazine prepared as described in EXAMPLE 2 (0.416 mmol) in methylene chloride was added DIEA (0.832 mmol) and commercially available neopentyl chloroformate (0.499 mmol). This solution was stirred for 2 hours at 25° C. and then the title compound was purified on preparative hpic and isolated via lyophilization. FAB-MS: calc: 395.5 found: 396.2. 1H-NMR (CD3OD): 8.9 ppm (s, 1H); 7.8 ppm (d, 2H); 7.5 ppm (s, 1H); 7.45 ppm (d, 2H); 5.65 ppm (s, 2H); 3.8 ppm (s, 2H); 3.45 ppm (s, 2H); 3.3 ppm (m, 4H): 2.3 ppm (m, 4H); 0.95 ppm (m, 9H).

Workup

customthe title compound was purified on preparative hpic and
customisolated via lyophilization

Sources & evidence

ORD record: ord-ed50947e92224891a11860e87b823c82
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355643B1

Reaction notes

Loading…