1-Hydroxybenzotriazole → Methyl cis(+/-)-3-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-propoxypiperidin-1-yl)benzoate

HRID 1425258Notes

Reaction equation

HRID 1425258 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH2:4][C@H:3]1[O:18][CH2:19][CH2:20][CH3:21].[Cl:22][C:23]1[N:24]=[C:25]([C:30](O)=[O:31])[NH:26][C:27]=1[CH2:28][CH3:29].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[Cl:22][C:23]1[N:24]=[C:25]([C:30]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]3[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=3)[C:11]([O:13][CH3:14])=[O:12])[CH2:4][C@H:3]2[O:18][CH2:19][CH2:20][CH3:21])=[O:31])[NH:26][C:27]=1[CH2:28][CH3:29]

Participants

5

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acid2×HCID 86648740HCID 86648740, compound

Product 1

HCID 86648739Methyl cis(+/-)-3-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-propoxypiperidin-1-yl)benzoate

Procedure

The same operation as in Example (1g) was performed using methyl cis(±)-3-(4-amino-3-propoxypiperidin-1-yl)benzoate obtained in Example (178b) (42.4 mg, 0.14 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained by the method described in Example (1d) (24.1 mg, 0.14 mmol), WSC hydrochloride (79.4 mg, 0.41 mmol) and HOBt (18.7 mg, 0.14 mmol), to obtain 35.5 mg of the title compound as a yellow oily substance (67%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-6e06e1c98858470381b80d9401cf0eef
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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