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

HRID 43493Notes

Reaction equation

HRID 43493 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:26](O)=[O:27])[NH:21][C:22]=1[CH2:23][CH2:24][CH3:25].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[Cl:17][C:18]1[N:19]=[C:20]([C:26]([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:27])[NH:21][C:22]=1[CH2:23][CH2:24][CH3:25]

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 67549025HCID 67549025, compound

Product 1

HCID 86648504tert-Butyl cis(+/-)-4-{[(4-chloro-5-propyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

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, 1.69 mmol), 4-chloro-5-propyl-1H-imidazole-2-carboxylic acid obtained in Example (46d) (0.16 g, 0.85 mmol), WSC hydrochloride (0.50 g, 2.58 mmol) and HOBT (0.12 g, 0.87 mmol), to obtain 0.32 g of the title compound as a white foamy substance (94%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-58c96173088441d79c88bdcbb555e5b8
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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