1,1'-Thiocarbonyldiimidazole → cis(+/-)-4-Chloro-5-ethyl-N-[1-(1H-imidazol-1-ylcarbonothioyl)-3-methoxypiperidin-4-yl]-1H-imidazole-2-carboxamide

HRID 43518Notes

Reaction equation

HRID 43518 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2CCN(C(OC(C)(C)C)=O)C[C@H]2OC)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Cl.[C:28]([O:31][CH2:32][CH3:33])(=O)C.[C:34]([N:41]1[CH:45]=[CH:44]N=C1)([N:36]1[CH:40]=[CH:39][N:38]=[CH:37]1)=[S:35]>CO>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:44][CH2:45][N:41]([C:34]([N:36]3[CH:40]=[CH:39][N:38]=[CH:37]3)=[S:35])[CH2:33][C@H:32]2[O:31][CH3:28])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 21866389Hydrogen chloride-ethyl acetateHCID 86648452tert-Butyl cis(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

Product 1

HCID 86648525cis(+/-)-4-Chloro-5-ethyl-N-[1-(1H-imidazol-1-ylcarbonothioyl)-3-methoxypiperidin-4-yl]-1H-imidazole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl cis(±)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylate obtained by the method described in Example (1g) (130 mg, 0.34 mmol) was dissolved in methanol (1 mL). A 4 N hydrochloric acid/ethyl acetate solution (3 mL) was added, and the mixture was stirred for 15 minutes. The reaction solution was concentrated under reduced pressure, and then the same operation as in Example (64a) was performed using 1,1′-thiocarbonyldiimidazole (81 mg, 0.45 mmol), to obtain the title compound. The resulting compound was used for the next reaction without purification.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0746a1d343cd4867831732b6b970cdc4
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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