Triethylamine → HCID 70664099, compound

HRID 1963082Notes

Reaction equation

HRID 1963082 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[N:10][N:9]2[C:12]([C:30]([N:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]3)=[O:31])=[C:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=3[CH3:29])[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:8]2[C:7]=1Cl)=[O:5])[CH3:2].C(N(CC)CC)C>C(O)C.C1COCC1.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[N:10][N:9]2[C:12]([C:30]([N:32]3[CH2:33][CH2:34][N:35]([C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[CH2:36][CH2:37]3)=[O:31])=[C:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=3[CH3:29])[C:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[C:8]2[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 67774159HCID 67774159, compound

Product 1

HCID 70664099HCID 70664099, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The compound of step 9 (1.880 g, 2.96 mmol) in 29.6 ml of ethanol/THF (1:1) was hydrogenated under a hydrogen pressure of 2 bar for 3.5 h at room temperature in the presence of 0.315 g of 10% palladium on charcoal and triethylamine (0.62 ml, 4.44 mmol). The catalyst was filtered off and the filtrate was washed with brine (50 ml), dried with magnesium sulfate, filtered and concentrated to dryness under reduced pressure. 1.67 g of the title compound were obtained as a yellow solid.

Workup

  1. customfor 3.5 h
  2. customat room temperature
  3. filtrationThe catalyst was filtered off
  4. washthe filtrate was washed with brine (50 ml)
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2e6aa282f1484d2190b1457e30038164
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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