Water → HCID 58431970, compound

HRID 2359010Notes

Reaction equation

HRID 2359010 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH2:22][C:11]3([O:16][C:15]4[CH:17]=[CH:18][CH:19]=[N:20][C:14]=4[NH:13][C:12]3=[S:21])[CH2:10][C:7]2=[N:8][CH:9]=1)([O-])=O.O.[Cl-].[NH4+]>CCO.CCOC(C)=O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]2[CH2:22][C:11]3([O:16][C:15]4[CH:17]=[CH:18][CH:19]=[N:20][C:14]=4[NH:13][C:12]3=[S:21])[CH2:10][C:7]2=[N:8][CH:9]=1

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 86657497HCID 86657497, compound

Product 1

HCID 58431970HCID 58431970, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-nitro-5,7-dihydrospiro[cyclopenta[b]pyridine-6,2′-pyrido[3,2-b][1,4]oxazine]-3′(4′H)-thione from Step E (628 mg, 2.0 mmol) in EtOH (16 mL) and EtOAc (8 mL) is treated successively with water (8 mL), iron powder (558 mg, 10 mmol) and ammonium chloride (53.5 mg, 1.0 mmol). The mixture is heated at reflux for 3 h and is then cooled to rt and filtered, washing the solids with additional EtOH. The filtrate is concentrated in vacuo and the residue is partitioned between EtOAc and saturated aqueous NaHCO3. The layers are separated and the organic layer is washed with brine, dried (Na2SO4), filtered and concentrated in vacua, The residue is purified by silica gel chromatography (gradient elution with 0-10% MeOH in CH2Cl2) to afford the title compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 h
  3. filtrationfiltered
  4. washwashing the solids with additional EtOH
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe residue is partitioned between EtOAc and saturated aqueous NaHCO3
  7. customThe layers are separated
  8. washthe organic layer is washed with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacua
  12. customThe residue is purified by silica gel chromatography (gradient elution with 0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-1821a2a5701f418b80c22db48425b1a3
Source dataset
uspto-grants-2014_04
Patent number
US08685965B2

Reaction notes

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