HCID 117690725, compound → HCID 89610028, compound

HRID 2174579Notes

Reaction equation

HRID 2174579 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[O:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[C:19]=2[CH3:20])([OH:14])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[CH3:20][C:19]1[C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[O:16][C:15]=1[C:11]1([OH:14])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 117690725HCID 117690725, compound

Product 1

HCID 89610028HCID 89610028, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of 3b (260 mg, 0.81 mmol) in methanol (5 ml) was added 10% Pd/C (130 mg). The mixture was degassed with nitrogen for 10 minutes and continued stirring at 20-35° C. under H2 gas atmosphere for 3 h. The progress of the reaction was monitored by TLC. The reaction mixture was filtered on celite bed, celite bed washed with methanol and resultant filtrate concentrated to get the desired product as a yellow waxy solid (180 mg, 96%). 1H NMR (400 MHz, DMSO-d6) δ 7.52 (dd, J=6.8, 2.0 Hz, 1H), 7.47-7.44 (m, 1H), 7.26-7.18 (m, 2H), 5.20 (bs, 1H), 2.92 (s, 1H), 2.73 (d, J=10.7 Hz, 2H), 2.44 (t, J=10.5 Hz, 2H), 2.34 (s, 3H), 2.15-2.07 (m, 2H), 1.84 (d, J=12.7 Hz, 2H); MS (ES) m/e 232.1 (M+H)+.

Workup

  1. customThe mixture was degassed with nitrogen for 10 minutes
  2. filtrationThe reaction mixture was filtered on celite bed, celite bed
  3. washwashed with methanol and resultant filtrate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-affa864010ec42fda00badb05b742d0e
Source dataset
uspto-grants-2015_06
Patent number
US09062002B2

Reaction notes

Loading…