Hydrochloric Acid → Benzyl 4-((3-chloropyrazin-2-yl)methylcarbamoyl)cyclohexyl(2-methoxyethyl)carbamate

HRID 245679Notes

Reaction equation

HRID 245679 reaction equation
[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([CH:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH2:19][CH2:20][O:21][CH3:22])[CH2:14][CH2:13]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1.C(N(CC)CC)C.[CH2:30]([O:37][C:38](ON1C(=O)CCC1=O)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.Cl>O1CCOCC1.O>[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([CH:12]2[CH2:17][CH2:16][CH:15]([N:18]([CH2:19][CH2:20][O:21][CH3:22])[C:38](=[O:39])[O:37][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:14][CH2:13]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 86674642N-((3-chloropyrazin-2-yl)methyl)-4-(2-methoxyethylamino)cyclohexanecarboxamide

Product 1

HCID 86674643Benzyl 4-((3-chloropyrazin-2-yl)methylcarbamoyl)cyclohexyl(2-methoxyethyl)carbamateYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-((3-chloropyrazin-2-yl)methyl)-4-(2-methoxyethylamino)cyclohexane-carboxamide (3.15 mmol, 1.03 g) in dioxane (10 ml) and water (10 ml) were added triethylamine (3.36 mmol, 0.47 ml) and N-(benzyloxycarbonyloxy)succinimide (3.31 mmol, 825 mg). After stirring for two hours at room temperature water and 2N hydrochloric acid (1.5 ml) were added and this mixture extracted twice with dichloromethane. The combined organic layers were washed with saturated aqueous sodium hydrogencarbonate solution, dried (sodium sulfate) and concentrated in vacuo to give benzyl 4-((3-chloropyrazin-2-yl)methylcarbamoyl)cyclohexyl(2-methoxyethyl)carbamate (1.45 g).

Workup

  1. additionwere added
  2. extractionthis mixture extracted twice with dichloromethane
  3. washThe combined organic layers were washed with saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2bf2a17b82e41d7a92229160888b3ae
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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