Water → HCID 178452047, compound

HRID 2114491Notes

Reaction equation

HRID 2114491 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:27]3[CH:26]=[CH:25][C:24]([C:28]#[N:29])=[CH:23][C:22]=3[O:21][C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[OH-:31].[NH4+:32].C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:27]3[CH:26]=[CH:25][C:24]([C:28](=[NH:32])[NH:29][OH:31])=[CH:23][C:22]=3[O:21][C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13908798HCID 13908798, compoundHCID 59809539HCID 59809539, compound2×

Product 1

HCID 178452047HCID 178452047, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(3-cyanophenoxazin-10-yl)-piperidine-1-carboxylic acid tert-butyl ester, 4a (130 mg; 0.33 mmol) in ethanol (3 mL) was added ammonium hydroxide hydrochloride (69 mg; 0.99 mmol) and potassium carbonate (91 mg; 0.66 mmol), and the mixture was heated to reflux for 16 h. The mixture was allowed to cool to rt, water (5 mL) was added, and the mixture was extracted with ethyl acetate (2×5 mL). The combined organic layers were dried over MgSO4, filtered, and evaporated, yielding 4-[3-(N-hydroxycarbamimidoyl)-phenoxazin-10-yl]-piperidine-1-carboxylic acid tert-butyl ester, 1b. The crude material was used as such in the next reaction. MS m/z (M+Na) 473.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 h
  3. extractionthe mixture was extracted with ethyl acetate (2×5 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4129ec8721f24f23872210b73783eff2
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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