Methanol → HCID 86687042, compound

HRID 1402181Notes

Reaction equation

HRID 1402181 reaction equation
[C:1]([C:5]1[NH:6][C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[C:8]([N:10]=O)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].CO>CCO.C(Cl)Cl.[Pd]>[C:1]([C:5]1[NH:6][C:7]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)=[C:8]([NH2:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 887MethanolHCID 86687041HCID 86687041, compound

Product 1

HCID 86687042HCID 86687042, compoundYield 68.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of Intermediate 51b (150 mg, 0.617 mmol) and Pd/C (10%, 15 mg) in EtOH (10 mL) was stirred at RT under H2 for 2 h. The flask was evacuated and purged with N2 thrice, then the mixture filtered through Celite, and the filter-cake washed with EtOH (10 mL). The combined organics were concentrated in vacuo to leave a red-brown gum. FCC, using 1-6% MeOH in DCM, gave the title compound as a yellow-orange gum (96.3 mg, 68%). LCMS (Method 3): Rt 2.26 min, m/z 230 [MH+].

Workup

  1. customThe flask was evacuated
  2. custompurged with N2 thrice
  3. filtrationthe mixture filtered through Celite
  4. washthe filter-cake washed with EtOH (10 mL)
  5. concentrationThe combined organics were concentrated in vacuo
  6. customto leave a red-brown gum

Sources & evidence

ORD record
ord-be91d1b4713c45f690d7d5e15b7b11fa
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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