Pyridine → HCID 25147807, compound

HRID 2380870Notes

Reaction equation

HRID 2380870 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].N1C=CC=CC=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:24]3[CH:25]=[CH:26][C:27]([NH2:29])=[CH:28][C:23]=3[O:22][C:21]([CH3:31])([CH3:30])[N:20]=2)=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[C:24]3[CH:25]=[CH:26][C:27]([NH:29][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:28][C:23]=3[O:22][C:21]([CH3:31])([CH3:30])[N:20]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 59443023HCID 59443023, compound

Product 1

HCID 25147807HCID 25147807, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methanesulfonyl chloride (55 μL) and pyridine (85 μL) were added dropwise to a solution of 4-(4-chlorophenyl)-2.2-dimethyl-2H-1,3-benzoxazin-7-ylamine (a compound of Reference Example 1, 101 mg) in chloroform (8 mL) and said mixture was stirred at room temperature for 2 days. The reaction solution was purified by column chromatography on silica gel (Chromatorex NH-silica gel, FUJI SILYSIA CHEMICAL LTD., Solvent: chloroform/methanol=100/0 to 90/10) and the obtained powder was suspended in diisopropyl ether. The resultant precipitates were collected by filtration and washed with diisopropyl ether to give the titled compound (112 mg) as a colorless powder.

Workup

  1. customThe reaction solution was purified by column chromatography on silica gel (Chromatorex NH-silica gel, FUJI SILYSIA CHEMICAL LTD., Solvent: chloroform/methanol=100/0 to 90/10)
  2. customThe resultant precipitates
  3. filtrationwere collected by filtration
  4. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-7dca9ab667ad48b681a2c1cf57eb9d8e
Source dataset
uspto-grants-2012_09
Patent number
US08258131B2

Reaction notes

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