HCID 69481484, compound → HCID 69482548, compound

HRID 2364271Notes

Reaction equation

HRID 2364271 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:44])=[C:14]([C:37]([NH:39][CH2:40][CH2:41][O:42][CH3:43])=[O:38])[C:15](=[O:36])[N:16]3[CH2:19][CH:20]3[CH2:25][CH2:24][N:23](C(OCC4C=CC=CC=4)=O)[CH2:22][CH2:21]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:44])=[C:14]([C:37]([NH:39][CH2:40][CH2:41][O:42][CH3:43])=[O:38])[C:15](=[O:36])[N:16]3[CH2:19][CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 69481484HCID 69481484, compound

Product 1

HCID 69482548HCID 69482548, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of Phenylmethyl 4-{[7-[(4-fluorophenyl)methyl]-4-hydroxy-3-({[2-(methyloxy)ethyl]amino}carbonyl)-2-oxo-1,5-naphthyridin-1(2H)-yl]methyl}-1-piperidinecarboxylate (18 mg, 0.03 mmol) in methanol (3 mL) was added palladium on carbon (10 wt %, 18 mg). Hydrogen was bubbled through the reaction mixture for several minutes and then the atmosphere was maintained with a balloon of hydrogen until the reaction was judged complete by LC/MS. The resultant suspension was filtered through a pad of Celite. The filtrate was concentrated in vacuo to give the title compound (10 mg, 71%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.23 (m, 1 H), 8.48 (s, 1 H), 7.36 (s, 1 H), 7.14 (dd, J=8.4, 5.4 Hz, 2 H), 6.99 (t, J=8.6 Hz, 2 H), 4.09 (s, 2 H), 4.02 (m, 2 H), 3.57 (m, 2 H), 3.53 (m, 2 H), 3.35 (s, 3 H), 3.14 (m, 2 H), 2.52 (m, 2 H), 1.78 (m, 1 H), 1.56-1.39 (m, 4 H); HRMS m/z calcd for C25H30N4O4F (M+H)+ 469.2251, found 469.2252.

Workup

  1. customHydrogen was bubbled through the reaction mixture for several minutes
  2. temperaturethe atmosphere was maintained with a balloon of hydrogen until the reaction
  3. filtrationThe resultant suspension was filtered through a pad of Celite
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-129154190625449b952b41187c7b69bd
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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