Pyridine → HCID 25183418, compound

HRID 2380872Notes

Reaction equation

HRID 2380872 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].N1C=CC=CC=1.[CH2:12]([C:14]1([CH2:32][CH3:33])[N:19]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:17]2[CH:27]=[CH:28][C:29]([NH2:31])=[CH:30][C:16]=2[O:15]1)[CH3:13]>C(Cl)(Cl)Cl>[CH2:32]([C:14]1([CH2:12][CH3:13])[N:19]=[C:18]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[C:17]2[CH:27]=[CH:28][C:29]([NH:31][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:30][C:16]=2[O:15]1)[CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 59442917HCID 59442917, compound

Product 1

HCID 25183418HCID 25183418, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

Methanesulfonyl chloride (63 μL) and pyridine (131 μL) were added dropwise to a solution of 2,2-diethyl-4-(4-fluorophenyl)-2H-1,3-benzoxazin-7-amine (a compound of Reference Example 4, 81 mg) in chloroform (5 mL), and the mixture was stirred at 40° C. overnight. The reaction mixture was purified by column chromatography on NH-silica gel (Chromatorex NH-silica gel, Solvent: chloroform/methanol=100/0 to 90/10), and the resultant powder was suspended in diisopropyl ether. The resultant precipitates were collected by filtration and washed with hexane-diisopropyl ether to give the titled compound (69 mg) as a colorless powder.

Workup

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

Sources & evidence

ORD record
ord-ac4569b4693145c59350c7bb5a32aee5
Source dataset
uspto-grants-2012_09
Patent number
US08258131B2

Reaction notes

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