Dimethylamine → HCID 10217417, compound

HRID 1268977Notes

Reaction equation

HRID 1268977 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.[CH3:32][NH:33][CH3:34].[OH2:35]>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:33]([CH3:34])[CH3:32])=[O:35])[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 674DimethylamineHCID 962WaterHCID 10175195HCID 10175195, compound

Product 1

HCID 10217417HCID 10217417, compoundYield 36%

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). Dimethylamine (0.250 ml, 40% in water, 2.2 mmol) and water (0.25 ml) were added and the reaction mixture was heated for 3 hours to 90° C. It was cooled to room temperature and the solvent was removed under vacuum. Chromatography on silica gel with dichloromethane/methanol (20:1) gave 74 mg (36%) of the title compound as a colourless solid.

Workup

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

Sources & evidence

ORD record
ord-bddbc1775ee849a1b748b848e99c7a7b
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

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