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

HRID 43504Notes

Reaction equation

HRID 43504 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 684188721,1-Dimethylethyl (3S,4R)-4-[[(5-chloro-4-ethyl-1H-imidazol-2-yl)carbonyl]amino]-3-methoxy-1-piperidinecarboxylateYield 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-8ec786062f264f51a65d33492c9ac397
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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