Water → HCID 10174333, compound

HRID 1268976Notes

Reaction equation

HRID 1268976 reaction equation
[O:1]=[S:2]1(=[O:31])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[C:23]([CH:25]=[C:26](Br)Br)[N:22]=[N:21]4)[O:16][C:15]3=[O:29])=[CH:10][C:9]=2[F:30])[CH2:4][CH2:3]1.[CH2:32]([NH:34][CH3:35])[CH3:33].[OH2:36]>CN(C=O)C>[O:1]=[S:2]1(=[O:31])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[C:23]([CH2:25][C:26]([N:34]([CH2:32][CH3:33])[CH3:35])=[O:36])[N:22]=[N:21]4)[O:16][C:15]3=[O:29])=[CH:10][C:9]=2[F:30])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 12219N-Methylethylamine2×HCID 10175195HCID 10175195, compound

Product 1

HCID 10174333HCID 10174333, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[4-(2,2-dibromoethenyl)-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (Example 25) (0.25 g, 0.43 mmol) was dissolved in DMF (1.5 ml). Ethylmethylamine (0.186 ml, 2.16 mmol) and water (0.5 ml) were added and the reaction mixture was heated for 2 hours to 90° C. More ethylmethylamine (0.2 ml, 2.33 mmol) was added and it was heated for another 1.5 hours. The reaction mixture was cooled to room temperature and the solvent was removed under vacuum. Chromatography on silica gel with toluene/ethanol (5:1) and then with hexanes/acetone (1:2) gave 27 mg (13%) of the title compound as a colourless solid.

Workup

  1. temperaturethe reaction mixture was heated for 2 hours to 90° C
  2. temperatureit was heated for another 1.5 hours
  3. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-86da9994379a4692987453a0faaa9e15
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

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