Hydrochloric Acid → HCID 135466501, compound

HRID 2114492Notes

Reaction equation

HRID 2114492 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:27]3[CH:26]=[CH:25][C:24]([C:28](=[NH:31])[NH:29]O)=[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)(C)(C)C.[C:32](N1C=CN=C1)(N1C=CN=C1)=[O:33].Cl.[O:45]1CCOCC1>>[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:27]3[CH:26]=[CH:25][C:24]([C:28]4[NH:29][C:32](=[O:33])[O:45][N:31]=4)=[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

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 682631,1'-CarbonyldiimidazoleHCID 178452047HCID 178452047, compound2×

Product 1

HCID 135466501HCID 135466501, compoundYield 14.4%

Conditions

Temperature
110 °C

Procedure

To a solution of 4-[3-(N-hydroxycarbamimidoyl)-phenoxazin-10-yl]-piperidine-1-carboxylic acid tert-butyl ester, 1b (0.13 g; 0.31 mmol) in dioxane (5 mL) was added 1,1′-carbonyldiimidazole (75 mg; 0.46 mmol), and the mixture was stirred at 110° C. for 4 hr. The mixture was allowed to cool to rt, and treated with 4N HCl in dioxane (5 mL). The mixture was stirred at rt for 16 hr and evaporated. The residue was suspended in methanol, and the solid was removed via filtration. The filtrate was purified via reverse phase HPLC (eluent gradient: 20 to 40% CH3CN in water containing 0.1% TFA) to yield 8.8 mg (14.4%) of 3-(10-piperidin-4-yl-10H-phenoxazin-3-yl)-4H-[1,2,4]oxadiazol-5-one, 2b as a TFA salt. MS m/z (MH+) 351.1.

Workup

  1. temperatureto cool to rt
  2. stirringThe mixture was stirred at rt for 16 hr
  3. customevaporated
  4. customthe solid was removed via filtration
  5. customThe filtrate was purified via reverse phase HPLC (eluent gradient: 20 to 40% CH3CN in water containing 0.1% TFA)

Sources & evidence

ORD record
ord-f57b58bb30c444d5a4483a09d8b3769d
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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