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

HRID 1424925Notes

Reaction equation

HRID 1424925 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:24](O)=[O:25])[NH:21][C:22]=1[CH3:23].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[Br:17][C:18]1[N:19]=[C:20]([C:24]([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:25])[NH:21][C:22]=1[CH3:23]

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 675486704-bromo-5-methyl-1H-imidazole-2-carboxylic acid

Product 1

HCID 86648474rel-1,1-Dimethylethyl (3R,4S)-4-[[(5-bromo-4-methyl-1H-imidazol-2-yl)carbonyl]amino]-3-methoxy-1-piperidinecarboxylateYield 83%

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) (0.88 g, 3.82 mmol), 4-bromo-5-methyl-1H-imidazole-2-carboxylic acid obtained in Example (31b) (0.37 g, 1.80 mmol), WSC hydrochloride (1.03 g, 5.37 mmol) and HOBT (0.25 g, 1.81 mmol), to obtain 0.63 g of the title compound as a white solid (83%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-47de3220d6c24a1a91f4c2551e5a6399
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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