Dimethylformamide → HCID 140520631, compound

HRID 639125Notes

Reaction equation

HRID 639125 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]=[CH2:13])=C[C:8]([O:14][CH3:15])=[CH:7][CH:6]=2.[OH:16]/[N:17]=[C:18]1/[C@H:19]([CH2:23][NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:20][NH:21][CH2:22]/1.C[N:36](C=O)C>>[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][N:21]1[CH2:22]/[C:18](=[N:17]\[OH:16])/[C@H:19]([CH2:23][NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:20]1)=[N:36][C:8]([O:14][CH3:15])=[CH:7][CH:6]=2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 57599587HCID 57599587, compoundHCID 140520633HCID 140520633, compound

Product 1

HCID 140520631HCID 140520631, compoundYield 18%

Conditions

Temperature
90 °C

Procedure

To 3-Fluoro-6-methoxy-4-vinyl-quinoline (0.554 g, 2.72 mmol) was added DMF (2.0 mL). Phenylmethyl {[(3S,4Z)-4-(hydroxyimino)-3-pyrrolidinyl]methyl}carbamate (0.66 g, 2.21 mmol) and TEA (0.76 mL, 5.44 mmol) were added to the mixture and the reaction was heated and stirred at 90 degrees C. for 18 hours. The solution was concentrated under reduced pressure and was chromatographed on silica gel to yield an oil (0.180 g, 18%). LCMS: m/z 468.4 (MH+).

Workup

  1. temperaturethe reaction was heated
  2. concentrationThe solution was concentrated under reduced pressure
  3. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-4b272163307a4d758b60fa41e7962242
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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