HCID 58877841, compound → HCID 54705118, compound

HRID 1664204Notes

Reaction equation

HRID 1664204 reaction equation
C([O:8][C:9]1[C:24](=[O:25])[N:13]2[CH2:14][CH2:15][O:16][CH2:17][C:18]3([CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:12]2=[N:11][C:10]=1[C:26]([NH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=1[N:37]1[C:41](=[O:42])[N:40]([CH3:43])[CH:39]=[N:38]1)=[O:27])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[F:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][NH:28][C:26]([C:10]2[N:11]=[C:12]3[C:18]4([CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[CH2:17][O:16][CH2:15][CH2:14][N:13]3[C:24](=[O:25])[C:9]=2[OH:8])=[O:27])=[C:31]([N:37]2[C:41](=[O:42])[N:40]([CH3:43])[CH:39]=[N:38]2)[CH:32]=1

Participants

5

Reactant 2

HCID 58877841HCID 58877841, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54705118HCID 54705118, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3′-(benzyloxy)-N-(4-fluoro-2-(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)benzyl)-4′-oxo-2,3,4′,5,6,6′,7′,9′-octahydrospiro[pyran-4,10′-pyrimido[1,2-d][1,4]oxazepine]-2′-carboxamide (0.093 g, 0.174 mmol) in ethyl acetate (5 mL) was added palladium on activated carbon (10%) (0.050 g) and the resulting mixture allowed to react under one atmosphere of hydrogen for 6 hours. The catalyst was removed by filtration and the filtrate was evaporated under reduce pressure to give a white solid. Recrystallization from hot ethanol afforded the title compound as a white solid (0.053 g, 68% yield): 1H NMR (400 MHz, CDCl3) δ 12.28 (1H, s), 8.95 (1H, brt), 7.66 (1H, dd, J=8.6, 6.1 Hz), 7.63 (1H, s), 7.22 (2H, dd, J=9.2, 2.8 Hz), 7.12 (2H, td, J=8.2, 2.8 Hz), 4.53 (2H, brs), 3.7-3.90 (10H, m), 3.43 (3H, s), 2.2-2.5 (2H, brm), 1.5-2.0 (2H, brm); LCMS (+ESI, M+H+) m/z 501.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customto give a white solid
  4. customRecrystallization from hot ethanol

Sources & evidence

ORD record
ord-ced077d5720e49d99de5fd2de1bcfbcc
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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