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

HRID 1424965Notes

Reaction equation

HRID 1424965 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][CH2:16][CH2:17][CH3:18].[Cl:19][C:20]1[N:21]=[C:22]([C:27](O)=[O:28])[NH:23][C:24]=1[CH2:25][CH3:26].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[Cl:19][C:20]1[N:21]=[C:22]([C:27]([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][CH2:16][CH2:17][CH3:18])=[O:28])[NH:23][C:24]=1[CH2:25][CH3:26]

Participants

5

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67548306Tert-butyl cis(+/-)-4-amino-3-propoxypiperidine-1-carboxylateHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acid2×

Product 1

HCID 86648505tert-Butyl cis(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-propoxypiperidine-1-carboxylate

Procedure

The same operation as in Example (1g) was performed using tert-butyl cis(±)-4-amino-3-propoxypiperidine-1-carboxylate obtained by the method described in Example (113d) (125.5 mg, 0.49 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained by the method described in Example (1d) (74 mg, 0.42 mmol), WSC hydrochloride (235 mg, 1.23 mmol) and HOBT (56 mg, 0.41 mmol), to obtain 145.6 mg of the title compound as a white foamy substance (83%).

Workup

  1. customobtained by the method
  2. customobtained by the method

Sources & evidence

ORD record
ord-071c4e0c43c542e6b8d778dff7846088
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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