Pyridine → HCID 25234154, compound

HRID 2421849Notes

Reaction equation

HRID 2421849 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][S:14][C:13]3[CH:17]=[CH:18][C:19]([C:21](Cl)=[O:22])=[CH:20][C:12]2=3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.N1C=CC=CC=1>ClCCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][S:14][C:13]3[CH:17]=[CH:18][C:19]([C:21]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[O:22])=[CH:20][C:12]2=3)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8083MorpholineHCID 86628744HCID 86628744, compound

Product 1

HCID 25234154HCID 25234154, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 4-(4-fluorophenylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carbonyl chloride (0.027 g, 72.6 μmol) in DCE (1 mL) was added morpholine (15.97 μL, 182 μmol) and pyridine (350 μL). The reaction was heated to 70° C. and stirred at that temperature for 16 hours. LCMS analysis of the reaction mixture indicated complete consumption of starting material. The resulting solid was purified by flash column chromatography using a gradient elution of hexanes with 0-60% EtOAc to provide (4-(4-fluorophenylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-6-yl)(morpholino)methanone (21.8 mg, 49.3 μmol, 88% yield for 2 steps) as off-white solid. LCMS (+ESI) m/z=423.5 [M+H]−.

Workup

  1. customconsumption of starting material
  2. customThe resulting solid was purified by flash column chromatography
  3. washa gradient elution of hexanes with 0-60% EtOAc

Sources & evidence

ORD record
ord-6f2755bc259b4d75b5d2e35f7f614189
Source dataset
uspto-grants-2011_06
Patent number
US07960376B2

Reaction notes

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