Diisopropylethylamine → HCID 86648556, compound

HRID 1425014Notes

Reaction equation

HRID 1425014 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[N:15]=[N+:16]=[N-:17].C(N(C(C)C)CC)(C)C.[Cl:27][C:28]1[N:29]=[C:30]([C:35](Cl)=[O:36])[NH:31][C:32]=1[CH2:33][CH3:34]>ClCCl>[N:15]([C@H:3]1[C@@H:2]([NH:1][C:35]([C:30]2[NH:31][C:32]([CH2:33][CH3:34])=[C:28]([Cl:27])[N:29]=2)=[O:36])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4]1)=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 866485554-Chloro-5-ethyl-1H-imidazole-2-carbonyl chlorideHCID 86648557HCID 86648557, compound

Product 1

HCID 86648556HCID 86648556, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl cis(±)-4-amino-3-azidopiperidine-1-carboxylate obtained in Example (81a) (about 0.29 mmol) was dissolved in dichloromethane (4 mL). Diisopropylethylamine (0.2 mL, 1.15 mmol) and 4-chloro-5-ethyl-1H-imidazole-2-carbonyl chloride obtained in Example (81b) (about 0.29 mmol) were added, followed by stirring for 2.5 hours. Dichloromethane was added to the reaction solution, and the organic layer was washed with 1 N hydrochloric acid, a 1 N aqueous sodium hydroxide solution and brine, and dried over anhydrous sodium sulfate. The residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=90/10, 70/30, 55/45) to obtain 90.4 mg of the title compound (78%).

Workup

  1. washthe organic layer was washed with 1 N hydrochloric acid
  2. dry with materiala 1 N aqueous sodium hydroxide solution and brine, and dried over anhydrous sodium sulfate
  3. customThe residue obtained by concentration under reduced pressure
  4. customwas purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=90/10, 70/30, 55/45)

Sources & evidence

ORD record
ord-d1c5a954a7184d659ab267a7d1b3945e
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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