Dimethylformamide → HCID 89690557, compound

HRID 1481880Notes

Reaction equation

HRID 1481880 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:23])[CH2:13][CH2:12]2)[C:8]([N+:24]([O-:26])=[O:25])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C)C=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH2:65][CH2:66][CH2:67][CH2:68][N:69]1[CH2:73][CH2:72][O:71][C:70]1=[O:74]>O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:23])[CH2:13][CH2:12]2)[C:8]([N+:24]([O-:26])=[O:25])=[CH:7][C:3]=1[C:4]([NH:65][CH2:66][CH2:67][CH2:68][N:69]1[CH2:73][CH2:72][O:71][C:70]1=[O:74])=[O:6]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 283953953-(3-Aminopropyl)oxazolidin-2-oneHCID 89690510HCID 89690510, compound

Product 1

HCID 89690557HCID 89690557, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 40 ml scintillation vial equipped with a magnetic stir bar and fitted with a nitrogen inlet, the 2-chloro-5-nitro-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid 1d (141.40 mg, 0.38 mmol) was taken up in clean, dry N,N-dimethylformamide (3.00 ml, 38.74 mmol) and the mixture was stirred together at room temperature under nitrogen atmosphere until all solids were taken up into solution. To this was added the HATU (171.70 mg, 0.45 mmol) followed by the N,N-diisopropylethylamine (0.20 ml, 1.15 mmol) and the mixture was once again stirred until all solids were in solution. Finally, the 3-(3-amino-propyl)-oxazolidin-2-one 15a (71.22 mg, 0.49 mmol) was added in one portion and the reaction was allowed to stir at room temperature overnight. The reaction was diluted with 10 ml of water and 10 ml of ethyl acetate. The layers were then separated and the product was extracted from the solution using ethyl acetate (3×15 ml). The organic phases were combined, washed with brine (1×25 ml) and saturated aqueous lithium chloride solution (2×25 ml). The solution was dried over Na2SO4; the solution was decanted and the solvent was removed under reduced pressure. The product was then purified using silica gel column chromatography, eluting a gradient of 100% dichloromethane to 10% MeOH in dichloromethane. The product, 2-chloro-5-nitro-N-[3-(2-oxo-oxazolidin-3-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide 15b (170.60 mg, 0.34 mmol), was isolated as an off-white solid and was carried on without further purification. LCMS=501 (M+H).

Workup

  1. customIn a 40 ml scintillation vial equipped with a magnetic stir bar
  2. customfitted with a nitrogen inlet
  3. stirringthe mixture was once again stirred until all solids
  4. stirringto stir at room temperature overnight
  5. customThe layers were then separated
  6. extractionthe product was extracted from the solution
  7. washwashed with brine (1×25 ml) and saturated aqueous lithium chloride solution (2×25 ml)
  8. dry with materialThe solution was dried over Na2SO4
  9. customthe solution was decanted
  10. customthe solvent was removed under reduced pressure
  11. customThe product was then purified
  12. washeluting a gradient of 100% dichloromethane to 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-4009d3cb15534936a7da0e41b58886fe
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

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