HCID 66993057, compound → HCID 52943944, compound

HRID 2199359Notes

Reaction equation

HRID 2199359 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH:4]=[C:5]1[C:10](=[O:11])[C:9](=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[CH2:8][NH:7][CH2:6]1>C(O)C.[Pd]>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][CH:9]1[C:10](=[O:11])[CH:5]([CH2:4][C:3]2[CH:20]=[CH:21][CH:22]=[CH:23][C:2]=2[F:1])[CH2:6][NH:7][CH2:8]1

Participants

4

Reactant 1

HCID 66993057HCID 66993057, compound

Product 1

HCID 52943944HCID 52943944, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound 1 (300 mg, 0.96 mmol) in ethanol, 10 mg of 5% Pd/C was added. The reaction mixture was stirred for 16 h under hydrogen gas at atmospheric pressure. Pd/C was filtered, and the solvent was evaporated to dryness. Compound 11 was obtained as a white solid (285 mg, 95% yield). Rf (30:70 methanol:chloroform)=0.20. 1H NMR (300 MHz, CDCl3): δ 7.25-6.90 (m, 8H, Ar—H), 3.60-2.50 (m, 10H, NCH2CHCH2). 13C NMR (75 MHz, CDCl3): 175.10, 161.05 (d, J=250.0), 131.34 (d, J=4.3), 128.68 (d, J=8.3), 124.28 (d, J=15.5), 115.48 (d, J=21.6), 48.55, 46.54, 25.52. ESI Mass calculated for C19H20F2NO (M+H)+316.15. found 316.20.

Workup

  1. filtrationPd/C was filtered
  2. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-1dc7240c27f94e0ca78546ff3135090e
Source dataset
uspto-grants-2016_06
Patent number
US09359196B2

Reaction notes

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