Water → 2-(4-Chloro-2-(tetrahydropyran-4-yl)aminonitrobenzen-5-yl)benzoxazole

HRID 74294Notes

Reaction equation

HRID 74294 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-:19])=[O:18])=[C:4](F)[CH:3]=1.[NH2:21][CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.O>C(#N)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]([N+:17]([O-:19])=[O:18])=[C:4]([NH:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4192234-AminotetrahydropyranHCID 674987962-(4-Chloro-2-fluoronitrobenzen-5-yl)benzoxazole

Product 1

HCID 674991902-(4-Chloro-2-(tetrahydropyran-4-yl)aminonitrobenzen-5-yl)benzoxazoleYield 21%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-(4-chloro-2-fluoronitrobenzen-5-yl)benzoxazole (see Working Example 112-1) (0.38 g, 1.3 mmol) in acetonitrile (8 mL) was added 4-aminotetrahydropyran (0.30 g, 2.9 mmol), and this was heated to reflux for 2 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered. The crystals obtained were purified by silica gel column chromatography to yield the title compound (0.10 g, 21% yield) as brown crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 2 hours
  3. filtrationthe precipitated crystals were filtered
  4. customThe crystals obtained
  5. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f2b515ed9ff24eb585bd659ce4125e1c
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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