1H-Imidazole-2-carboxylic acid → tert-Butyl cis(+/-)-4-[(1H-imidazol-2-ylcarbonyl)amino]-3-methoxypiperidine-1-carboxylate

HRID 43436Notes

Reaction equation

HRID 43436 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].[NH:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22](O)=[O:23].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C>[NH:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]([NH:1][C@H:2]1[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]1[O:15][CH3:16])=[O:23]

Participants

5

Reactant 3

HCID 5743211H-Imidazole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57362389(3R,4S)-4-Amino-1-boc-3-methoxypiperidine2×

Product 1

HCID 86648456tert-Butyl cis(+/-)-4-[(1H-imidazol-2-ylcarbonyl)amino]-3-methoxypiperidine-1-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

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) (0.20 g, 0.87 mmol), 1H-imidazole-2-carboxylic acid obtained in Example (3a) (91 mg, 0.81 mmol), WSC hydrochloride (0.36 g, 1.88 mmol) and DMAP (10 mg, 0.083 mmol), to obtain 138 mg of the title compound as a white solid (58%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-ce31ef13e58f4c2e8194f2fc1e24d25f
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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