Dichloromethane → HCID 70874384, compound

HRID 2172279Notes

Reaction equation

HRID 2172279 reaction equation
O1CCOCC1.Cl.C(Cl)Cl.C(OC([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C@@H:32]3[O:37][C:36]4=[N:38][C:39]([N+:41]([O-:43])=[O:42])=[CH:40][N:35]4[CH2:34][CH2:33]3)=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)=O)(C)(C)C>C(OCC)(=O)C>[N+:41]([C:39]1[N:38]=[C:36]2[N:35]([CH:40]=1)[CH2:34][CH2:33][C@H:32]([CH2:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([N:21]3[CH2:22][CH2:23][NH:18][CH2:19][CH2:20]3)=[CH:25][CH:26]=1)[O:37]2)([O-:43])=[O:42]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 204431481,4-Dioxane hydrochlorideHCID 70874211HCID 70874211, compound

Product 1

HCID 70874384HCID 70874384, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 4 N hydrochloric acid 1,4-dioxane solution (22 ml) was gradually added to a methylene chloride (22 ml) suspension of 4-[4-((R)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-ylmethoxy)phenyl]piperazine-1-carboxylic acid tert-butyl ester (4.51 g), and the mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate and the precipitate was collected by filtration. The solid thus obtained was subjected to triturate with ethanol, collected by filtration and then dried. Hydrochloride of the title product was dissolved in water and neutralized using a 5 N sodium hydroxide aqueous solution under ice cooling, followed by stirring. The precipitate was collected by filtration and dried at 60° C. to afford the title compound as a yellow powder (3.0 g).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customThe solid thus obtained
  3. customto triturate with ethanol
  4. filtrationcollected by filtration
  5. customdried
  6. dissolutionHydrochloride of the title product was dissolved in water
  7. stirringby stirring
  8. filtrationThe precipitate was collected by filtration
  9. customdried at 60° C.

Sources & evidence

ORD record
ord-2f9d9a517b234a528f68be471ddc37f3
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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