1-Hydroxybenzotriazole → tert-Butyl trans(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-hydroxypiperidine-1-carboxylate

HRID 43533Notes

Reaction equation

HRID 43533 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[OH:15].[Cl:16][C:17]1[N:18]=[C:19]([C:24](O)=[O:25])[NH:20][C:21]=1[CH2:22][CH3:23].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[Cl:16][C:17]1[N:18]=[C:19]([C:24]([NH:1][C@@H:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:4][C@H:3]2[OH:15])=[O:25])[NH:20][C:21]=1[CH2:22][CH3:23]

Participants

5

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10727458rac-tert-butyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylateHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acid2×

Product 1

HCID 86648545tert-Butyl trans(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-hydroxypiperidine-1-carboxylateYield 76%

Procedure

The same operation as in Example (1g) was performed using tert-butyl trans(±)-4-amino-3-hydroxypiperidine-1-carboxylate obtained in Example (77a) (510 mg, 2.36 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained by the method described in Example (1d) (440 mg, 2.14 mmol), WSC hydrochloride (1.2 g, 6.26 mmol) and HOBT (284 mg, 2.10 mmol), to obtain 604.1 mg of the title compound as a white solid (76%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-afb0b8c620e74c64b2345c4edc77a07f
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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