1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-Butyl cis(+/-)-4-{[(4,5-dibromo-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

HRID 1424903Notes

Reaction equation

HRID 1424903 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[Br:23].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C>[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[Br:23]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 126303334,5-dibromo-1H-imidazole-2-carboxylic acidHCID 57362389(3R,4S)-4-Amino-1-boc-3-methoxypiperidine2×

Product 1

HCID 86648455tert-Butyl cis(+/-)-4-{[(4,5-dibromo-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylateYield 72%

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) (300 mg, 1.30 mmol), 4,5-dibromoimidazole-2-carboxylic acid obtained in Example (2a) (300 mg, 1.11 mmol), WSC hydrochloride (460 mg, 2.40 mmol) and DMAP (50 mg, 0.41 mmol), to obtain 384 mg of the title compound as a white solid (72%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-ac335fe48ed745a38e5f9471bc526b10
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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