Diisopropylethylamine → (1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-methanone

HRID 548812Notes

Reaction equation

HRID 548812 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[N:20]=[N:19][C:18]([C:21]([OH:23])=O)=[CH:17][CH:16]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH:55]1[CH2:60][CH2:59][S:58](=[O:62])(=[O:61])[CH2:57][CH2:56]1>CN(C=O)C.O>[O:61]=[S:58]1(=[O:62])[CH2:59][CH2:60][N:55]([C:21]([C:18]2[N:19]=[N:20][C:15]([O:14][CH2:13][C:3]3[C:4]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)=[N:5][O:6][C:2]=3[CH3:1])=[CH:16][CH:17]=2)=[O:23])[CH2:56][CH2:57]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6484228Thiomorpholine 1,1-dioxideHCID 665989756-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid

Product 1

HCID 67158014(1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-methanoneYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (200 mg, 0.64 mmol) in DMF (8 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (227 mg, 0.70 mmol), N,N-diisopropyl ethyl amine (550 μL, 3.2 mmol) and thiomorpholine 1,1-dioxide (0.104 g, 0.77 mmol). The resulting reaction mixture was stirred for 30 min at room temperature and diluted with water. The mixture was then extracted with ethyl acetate and the combined organic layers washed with aqueous sodium carbonate (saturated) and dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 6:4) afforded the title compound (176 mg, 63%) as a white solid. MS: m/e=429.2 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. extractionThe mixture was then extracted with ethyl acetate
  3. washthe combined organic layers washed with aqueous sodium carbonate (saturated)
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 6:4)

Sources & evidence

ORD record
ord-714c2462f5bd4bcbb8174a966197cab6
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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