Diethyl Ether → HCID 10450532, compound

HRID 457573Notes

Reaction equation

HRID 457573 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[O:13][C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[N:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C(OCC)C>CO.[Pd]>[CH3:27][N:24]1[CH2:23][CH2:22][N:21]([C:18]2[CH:19]=[CH:20][C:15]([NH:14][C:12]3[O:13][C:9]([C:5]4[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=4)=[CH:10][N:11]=3)=[CH:16][CH:17]=2)[CH2:26][CH2:25]1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 10451418HCID 10451418, compound

Product 1

HCID 10450532HCID 10450532, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of the title compound of Example 4 (0.20 g, 0.45 mmol) in methanol (50 mL) was added palladium on carbon (10% w/w, 0.1 g) and was hydrogenated at 50 psi for 12 h. The catalyst was removed by filtration and the solvent was evaporated from the filtrate to leave a tan solid. Trituration with diethyl ether afforded a solid that was collected by filtration and dried under vacuum to leave the title compound (0.16 g, 96%). 1H NMR (400 MHz, d6-DMSO): δ 2.20 (s, 3H), 2.43 (m, 4H), 3.03 (m, 4H), 6.62 (d, J=9.16, 1H), 6.90 (m, 3H), 6.95 (d, J=7.69, 1H), 7.17 (t, J=7.87, 1H), 7.29 (s, 1H), 7.46 (d, J=8.61, 2H), 9.95 (s, 1H). MS (APCI, m/z)=336 (m+1).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated from the filtrate
  3. customto leave a tan solid
  4. filtrationthat was collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-5e99290ea9ba498592329b758d6cefbb
Source dataset
uspto-grants-2007_03
Patent number
US07189712B2

Reaction notes

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