Diisopropylethylamine → (S)-N'-(6-Chloropyridazin-3-yl)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzohydrazide

HRID 525380Notes

Reaction equation

HRID 525380 reaction equation
[CH3:1][C:2]1([CH3:23])[O:6][C:5](=[O:7])[N:4]([C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=2)[C@H:3]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:57][C:58]1[N:59]=[N:60][C:61]([NH:64][NH2:65])=[CH:62][CH:63]=1>CN(C=O)C.O>[Cl:57][C:58]1[N:59]=[N:60][C:61]([NH:64][NH:65][C:12](=[O:13])[C:11]2[CH:10]=[CH:9][C:8]([N:4]3[C@@H:3]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:2]([CH3:23])([CH3:1])[O:6][C:5]3=[O:7])=[CH:16][CH:15]=2)=[CH:62][CH:63]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1007873-Chloro-6-hydrazinopyridazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71681650(S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoic acid

Product 1

HCID 89814317(S)-N'-(6-Chloropyridazin-3-yl)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzohydrazide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(S)-4-(5,5-Dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoic acid (400 mg, 1.285 mmol) was dissolved in DMF (2.57 mL) at room temperature. To the reaction mixture, was successively added N-ethyl-N-isopropylpropan-2-amine (670 μL, 3.85 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (489 mg, 1.285 mmol, commercially available from Sigma-Aldrich, Milwaukee, Wis.) and 3-chloro-6-hydrazinylpyridazine (186 mg, 1.285 mmol). The vial was sealed and immersed in a 55° C. oil bath. After stirring overnight, LC-MS indicated complete conversion to the product. After cooling to room temperature, the reaction mixture was transferred to water in a flask in an ice/water bath. The solution was extracted w with DCM (3×50 mL). The combined organic layers were then washed with water (2×50 mL) and brine (50 mL). The organic layer was dried over Na2SO4. The solution was then filtered and concentrated under reduced pressure to give the product as a yellow solid. The product thus obtained was was used in the next step without further purification. m/z (ESI) 438.0 (M+H)+.

Workup

  1. customThe vial was sealed
  2. customimmersed in a 55° C.
  3. extractionThe solution was extracted w with DCM (3×50 mL)
  4. washThe combined organic layers were then washed with water (2×50 mL) and brine (50 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationThe solution was then filtered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-56f853566c554127af9526a3e2c1427c
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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