Hydrochloric Acid → HCID 178491153, compound

HRID 1934682Notes

Reaction equation

HRID 1934682 reaction equation
Cl.C(OC([NH:9][C@@H:10]1[CH2:15][CH2:14][C@H:13]([NH:16][C:17]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][C:18]=2[C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=2)=[O:20])[CH2:12][CH2:11]1)=O)(C)(C)C>C(OCC)(=O)C>[NH2:9][C@@H:10]1[CH2:15][CH2:14][C@H:13]([NH:16][C:17]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][C:18]=2[C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=2)=[O:20])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178491158HCID 178491158, compound

Product 1

HCID 178491153HCID 178491153, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

4N-Hydrogen chloride solution in ethyl acetate (2 mL) was added to a solution of 2-[cis-4-(N-tert-butoxycarbonylamino)cyclohexylamino]-N-(3,4-dimethoxybenzyl)-5-nitrobenzamide (270 mg) in ethyl acetate (1 mL). The mixture was stirred for 2 hours at ambient temperature. The reaction mixture was concentrated in vacuo. To the residue were added an aqueous saturated sodium bicarbonate solution and ethyl acetate. The appeared precipitates were collected by filtration and washed with ethyl acetate and water successively to give 2-(Cis-4-aminocyclohexylamino)-N-(3,4-dimethoxybenzyl)-5-nitrobenzamide (77 mg) as yellow powders. The filtrate was separated, and the aqueous layer was extracted with chloroform. The combined organic layer was dried over magnesium sulfate and concentrated in vacuo to give a second crop (137.8 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionTo the residue were added an aqueous saturated sodium bicarbonate solution and ethyl acetate
  3. customThe appeared precipitates
  4. filtrationwere collected by filtration
  5. washwashed with ethyl acetate and water successively

Sources & evidence

ORD record
ord-60c2c634713d417fa8682088180fd795
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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