Dimethylformamide → HCID 67236728, compound

HRID 2364850Notes

Reaction equation

HRID 2364850 reaction equation
[F:1][C:2]1([F:17])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=2)[CH2:4][CH2:3]1.C1COCC1.CN(C=O)C>[Ni].O>[F:17][C:2]1([F:1])[CH2:7][CH2:6][N:5]([C:8]2[N:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 67237449HCID 67237449, compound

Product 1

HCID 67236728HCID 67236728, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

The product from Example 135A (4.56 g, 18.75 mmol) and solvent THF (20 mL)/DMF were added to Ra—Ni 2800, water slurry (4.56 g, 78 mmol) in a 250 mL SS pressure bottle and stirred for 2 hr at 30 psi and ambient temperature. The mixture was filtered through a nylon membrane and washed with MeOH. The filtrate was concentrated and dried under vacuum to afford the title compound (3.40 g, 85%). 1H NMR (400 MHz, DMSO-D6) δ 2.03-1.88 (m, 4H), 3.49-3.38 (m, 4H), 4.61 (s, 2H), 6.73 (d, J=8.8, 1H), 6.93 (dd, J=2.9, 8.8, 1H), 7.61 (d, J=2.6, 1H). MS (ESI) m/z 214 (M+H+).

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b5839a30c1834842a1f8e800d4947f69
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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