HCID 66745729, compound → HCID 54588614, compound

HRID 2169889Notes

Reaction equation

HRID 2169889 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][C:14]([NH:17][C:18](=[O:38])[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH2:28][CH2:29][O:30]CC3C=CC=CC=3)[CH:20]=2)([CH3:16])[CH3:15])[N:5]=[C:4]([CH3:39])[C:3]=1[C:40]([OH:42])=[O:41]>CCO.CCOC(C)=O.[Pd]>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][C:14]([NH:17][C:18](=[O:38])[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH2:28][CH2:29][OH:30])[CH:20]=2)([CH3:15])[CH3:16])[N:5]=[C:4]([CH3:39])[C:3]=1[C:40]([OH:42])=[O:41]

Participants

4

Reactant 1

HCID 66745729HCID 66745729, compound

Product 1

HCID 54588614HCID 54588614, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 4-amino-5-(2-(3-(2-(benzyloxy)ethoxy)-5-methoxybenzamido)-2-methylpropoxy)-2-methylquinoline-3-carboxylic acid (Example 38a, 237 mg, 0.5 mmol) in EtOH/EtOAc (1:1, 20 mL) was added 10% Pd/C (wet, 50 mg). The suspension was then stirred under an atmosphere of hydrogen at room temperature overnight. The Pd/C was filtered off, and the filtrate was concentrated. The residue was purified by HPLC (eluent: 10-100% MeOH in H2O) to give the title compound as an off-white solid (152 mg, 63%). 1H NR (400 MHz, DMSO-d6) δ 1.49 (s, 6H), 2.75 (s, 3H), 3.68 (t, J=5.2 Hz, 2H), 3.73 (s, 3H), 3.99 (t, J=5.2 Hz, 1H), 4.47 (s, 2H), 6.57 (s, 1H), 6.88 (s, 1H), 6.96 (s, 1H), 7.06 (d, J=7.6 Hz, 1H), 7.28 (d, J=8 Hz, 1H), 7.67 (t, J=8 Hz, 1H), 8.14 (s, 1H). MS 484 (MH+).

Workup

  1. filtrationThe Pd/C was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by HPLC (eluent: 10-100% MeOH in H2O)

Sources & evidence

ORD record
ord-f256eb2b45d84a5699018520d8880513
Source dataset
uspto-grants-2015_06
Patent number
US09049878B2

Reaction notes

Loading…