1-Hydroxybenzotriazole → rel-1,1-Dimethylethyl (3R,4S)-4-[[(5-bromo-4-ethyl-1H-imidazol-2-yl)carbonyl]amino]-3-methoxy-1-piperidinecarboxylate

HRID 43451Notes

Reaction equation

HRID 43451 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[O:15][CH3:16].[Br:17][C:18]1[N:19]=[C:20]([C:25](O)=[O:26])[NH:21][C:22]=1[CH2:23][CH3:24].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[Br:17][C:18]1[N:19]=[C:20]([C:25]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][C@H:3]2[O:15][CH3:16])=[O:26])[NH:21][C:22]=1[CH2:23][CH3:24]

Participants

5

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57362389(3R,4S)-4-Amino-1-boc-3-methoxypiperidine2×HCID 675491255-Bromo-4-ethyl-1H-imidazole-2-carboxylic acid

Product 1

HCID 86648469rel-1,1-Dimethylethyl (3R,4S)-4-[[(5-bromo-4-ethyl-1H-imidazol-2-yl)carbonyl]amino]-3-methoxy-1-piperidinecarboxylateYield 92%

Procedure

The same operation as in Example (1g) was performed using tert-butyl cis(±)-4-amino-3-methoxypiperidine-1-carboxylate obtained by the method described in Example (1e) (0.39 g, 1.67 mmol), 4-bromo-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (25b) (0.18 g, 0.82 mmol), WSC hydrochloride (0.49 g, 2.53 mmol) and HOBT (0.11 g, 0.84 mmol), to obtain 0.33 g of the title compound as a white solid (92%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-5de31555ba3c4c2cab85e7f3e12eff76
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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