1-Hydroxybenzotriazole → tert-Butyl (3S,4R)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

HRID 1424975Notes

Reaction equation

HRID 1424975 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].[Cl: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>>[Cl: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 25417269(3S,4R)-tert-Butyl 4-amino-3-methoxypiperidine-1-carboxylateHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acid2×

Product 1

HCID 68418872tert-Butyl (3S,4R)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylateYield 72%

Procedure

The same operation as in Example (1g) was performed using tert-butyl (3S,4R)-4-amino-3-methoxypiperidine-1-carboxylate obtained in Example (56a) (224.4 mg, 0.96 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid synthesized by the method described in Example (1d) (140 mg, 0.80 mmol), WSC hydrochloride (440 mg, 2.29 mmol) and HOBT (110 mg, 0.81 mmol), to obtain 222.4 mg of the title compound as a white solid (72%).

Workup

  1. customsynthesized by the method

Sources & evidence

ORD record
ord-30531389b3924818996f50af1d6128af
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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