2-(4-Chloro-2-(tetrahydropyran-4-yl)aminonitrobenzen-5-yl)benzoxazole → HCID 67498666, compound

HRID 74295Notes

Reaction equation

HRID 74295 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][C:5]([N+:17]([O-])=O)=[C:4]([NH:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:3]=1>[Fe].C(O)(=O)C>[Cl:1][C:2]1[C:7]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][C:5]([NH2:17])=[C:4]([NH:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:3]=1

Participants

4

Reactant 1

HCID 674991902-(4-Chloro-2-(tetrahydropyran-4-yl)aminonitrobenzen-5-yl)benzoxazole

Product 1

HCID 67498666HCID 67498666, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To 2-(4-chloro-2-(tetrahydropyran-4-yl)aminonitrobenzen-5-yl)benzoxazole (see Working Example 112-2) (0.10 g, 0.8 mmol) was added iron powder (0.33 g, 5.8 mmol) and acetic acid (50 mL), and this was heated to reflux for 2 hours. After the reaction solution cooled, this was filtered through Celite and concentrated, and the residue obtained was purified by silica gel column chromatography to yield the title compound (0.06 g, 65% yield) as a reddish-brown solid.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter the reaction solution cooled
  4. filtrationthis was filtered through Celite
  5. concentrationconcentrated
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-51ba33be36ca41aba9b8486e6733c2a6
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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