Dimethylformamide → HCID 131731063, compound

HRID 1908685Notes

Reaction equation

HRID 1908685 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]([C@H:13]2[CH2:15][C@@H:14]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:12])[CH3:9])=[CH:4][CH:3]=1.Cl.[CH3:23]N(C)O.[C:27](=[O:30])([O-])[O-].[Cs+].[Cs+].CN([CH:36]=[O:37])C>[Cl-].[Na+].O>[O:37]1[CH2:36][CH:27]([O:30][C:3]2[CH:4]=[C:5]([C@@H:8]([NH:10][C:11]([C@H:13]3[CH2:15][C@@H:14]3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:12])[CH3:9])[CH:6]=[N:7][CH:2]=2)[CH2:23]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 71487163HCID 71487163, compound2×

Product 1

HCID 131731063HCID 131731063, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

(1S,2S)-2-Phenyl-cyclopropanecarboxylic acid [(S)-1-(6-chloro-pyridin-3-yl)-ethyl]-amide (Compound 18) (2.00 g, 6.65 mmol) was dissolved in DMF (40 ml). N,N-dimethylhydroxylaminehydrochloride (5.00 g, 51.2 mmol) and dicesium carbonate (25 g, 76.7 mmol) were added and the mixture was heated at 95 C 3 days. The mixture was poured out into brine and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4) and was filtered and then evaporated to dryness. The residue was transferred to a silica gel column and eluded with EtOAc to give Compound 50 as a solid. This solid was dissolved in a mixture of THF (10 ml), EtOAc (10 ml) and heptanes (10 ml). The mixture was concentrated to approx. 10 ml volume and this solution was cooled in an ice/water bath. A white precipitate formed. The solids was collected by filtration and dried in vacuo to give the title compound as a white solid (0.044 g, 2%). 1H-NMR (500 MHz, DMSO) δ 8.43 (d, 1H), 8.02 (s, 1H), 7.45 (d, 1H), 7.25 (m, 2H), 7.17 (m, 1H), 7.10 (d, 2H), 6.61 (d, 1H), 4.83 (m, 1H), 3.98 (m, 6H), 2.19 (m, 1H), 1.90 (m, 1H), 1.35 (m, 4H), 1.21 (m, 1H). LC-MS (m/z) 310.2 (MH+), tR=0.46 min (method B). Mp=171-181 C.

Workup

  1. temperaturethe mixture was heated at 95 C 3 days
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationwas filtered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-68d70c629bed4913b64f2ff45e299b6c
Source dataset
uspto-grants-2013_12
Patent number
US08598213B2

Reaction notes

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