HCID 57905092, compound → HCID 57904795, compound

HRID 1093150Notes

Reaction equation

HRID 1093150 reaction equation
[CH2:1]1[CH:6]2[CH2:7][N:8]3[C:13](=[O:14])[C:12]([OH:15])=[C:11]([C:16]([NH:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)=[O:17])[N:10]=[C:9]3[C:3]([NH:27]C(OCC3C=CC=CC=3)=O)([CH2:4][O:5]2)[CH2:2]1>CO.[Pd]>[CH2:1]1[CH:6]2[CH2:7][N:8]3[C:13](=[O:14])[C:12]([OH:15])=[C:11]([C:16]([NH:18][CH2:19][C:20]4[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=4)=[O:17])[N:10]=[C:9]3[C:3]([NH2:27])([CH2:4][O:5]2)[CH2:2]1

Participants

4

Reactant 1

HCID 57905092HCID 57905092, compound

Product 1

HCID 57904795HCID 57904795, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of benzyl (2-((4-fluorobenzyl)carbamoyl)-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-7,10-(epoxymethano)pyrimido[1,2-a]azepin-10(4H)-yl)carbamate (110 mg, 0.216 mmol) in methanol (3 mL) was added 10% Pd/C (115 mg, 0.108 mmol) and the mixture stirred under 1 atm H2 for 18 h. The mixture was then filtered through a pad of CELITE® and the pad washed with ethyl acetate. The filtrate was concentrated to afford the title compound (70 mg, 86% yield) as a light yellow solid. 1H NMR (500 MHz, CDCl3) δ: 7.84 (brs, 1H), 7.29 (dd, 2H, J=8.09 & 5.34 Hz), 7.02 (t, 2H, J=8.55 Hz), 4.56 (d, 2H, J=6.1 Hz), 4.43-4.50 (m, 2H), 4.04-4.11 (m, 2H), 3.87 (d, 1H, J=10.99 Hz), 2.28-2.32 (m, 2H), 1.98-2.09 (m, 3H), 1.55-1.61 (m, 1H). LCMS (M+H)=375.2.

Workup

  1. filtrationThe mixture was then filtered through a pad of CELITE®
  2. washthe pad washed with ethyl acetate
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7220fcf783f84d07bc573633da120e71
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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